ChemicalBook CAS DataBase List 3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one

3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one synthesis

5synthesis methods

Product Name:3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one
CAS Number:86499-96-9
Molecular formula:C10H10BrNO
Molecular Weight:240.1

The preparation of 3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one is as follows:10 parts by weight of the heated melted polyphosphoric acid was added to the drying kettle, With stirring, The above 2-bromo-3,4-dihydro-N-hydroxy- (2H) -naphthalimide was added in portions at a temperature of 60 ° C, Insulation reaction for 20 hours; The reaction solution was added dropwise to 12.5 parts by weight of water to carry out hydrolysis, Still Washed to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one crude; 10 parts by weight of methanol and 0.1 part by weight of activated carbon were added, Heating decolorization, After filtration, the filtrate was cooled to 10 ° C for 20 hours, centrifuged, washed and dried to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one. The purity of the product was 3, 10-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one as high as 99.6% and the yield was as high as 98%.

1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

4424-80-0
141 suppliers
$25.00/1g

3-Bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one

86499-96-9
269 suppliers
$14.00/1g

Yield:86499-96-9 70.1%

Reaction Conditions:

Stage #1:2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one with phosphorus pentachloride;iodine in chloroform at 0; for 0.5 h;
Stage #2: with bromine in chloroform at 0 - 20; for 4 h;Refluxed;

Steps:

4.A(2)
A solution of Part A(1) compound (1.0 g, 6.20 mmoles) in dry CHCl₃(15 ml) was cooled down to 0° C. (ice-salt bath), treated with PCl₅(1.5 g, 7.20 mmoles) followed by I₂(15 mg) then stirred at 0° C. under argon for 30 minutes. The yellow solution was treated with Br₂(0.39 ml or 1.2 g, 7.51 mmoles), warmed up to room temperature and refluxed under argon for 4.0 hours. The mixture was then poured into ice-water (20 g), stirred and the phases were separated, washing the aqueous phase with CHCl₃(25 ml). The combined organic extracts were washed with H₂O (5.0 ml), dried (anhydrous MgSO₄), filtered, evaporated to dryness and dried in vacuo. The crude product mixture was chromatographed on a silica gel column (Merck, 70 g), eluting the column with EtOAc:Hexane (1:9) to give title compound as off-white precipitates (1.137 g., m.pt. 170-172°, 70.1%) with consistent ¹H-NMR and ¹³C-NMR spectral data. [00180] TLC: R_f0.13 (Silica gel; EtOAc:Hexane-1:4; UV).

References:

Bristol-Myers Squibb Company US6777550, 2004, B1 Location in patent:Page column 28

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