(S)-2-Bromo-1-(3-bromophenyl)ethan-1-ol synthesis
- Product Name:(S)-2-Bromo-1-(3-bromophenyl)ethan-1-ol
- CAS Number:1098108-56-5
- Molecular formula:C8H8Br2O
- Molecular Weight:279.9565
18523-22-3
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Yield:1098108-56-5 100%
Reaction Conditions:
with dimethylsulfide borane complex;(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole in tetrahydrofuran at 0 - 20; for 12 h;
Steps:
29 ^-2-Bromo-l-(3-bromophenyl)ethanol (29.2)
To a stirred solution of ()-l-methyl-3,3-diphenylhexahydropyrrolo[l,2- c][l,3,2]oxazaborole (1 g, 3.61 mmol) in THF (50 mL) was added BH3-DMS (10 M, 2.5 mL, 25.3 mmol) at 0 °C. The mixture was stirred for 0.5 h at 0 °C. To the reaction mixture was added a solution of 2-bromo-l-(3-bromophenyl)ethanone (10 g, 36.1 mmol) in THF (30 mL) dropwise at 0 °C. The mixture was stirred for 12 h at rt. To the mixture was added MeOH dropwise (the mixture was bubbled). Stop the adding of MeOH after the mixture didn't bubble. Then the mixture was concentrated and purified by column (PE/EA = 50/1 to 20/1 to 10/1 to 5/1) to give ()-2-bromo-l- (3-bromophenyl)ethanol (10 g, 100 % yield) as a white solid. MR (400 MHz, CDC13) δ 7.56 (t, J = 1.8 Hz, 1 H), 7.47-7.45 (m, 1 H), 7.32-7.30 (m, 1 H), 7.26-7.22 (m, 1 H), 4.90 (d, J = 8.7 Hz, 1 H), 3.63 (dd, J= 10.5, 3.4 Hz, 1 H), 3.51 (dd, J = 10.5, 8.8 Hz, 1 H), 2.68 (d, J = 1.6 Hz, 1 H).
References:
WO2019/60693,2019,A1 Location in patent:Paragraph 00407-00408
40422-70-6
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