ChemicalBook CAS DataBase List 1-Bromo-2-bromomethyl-4-nitro-benzene

1-Bromo-2-bromomethyl-4-nitro-benzene synthesis

5synthesis methods

Product Name:1-Bromo-2-bromomethyl-4-nitro-benzene
CAS Number:939-82-2
Molecular formula:C7H5Br2NO2
Molecular Weight:294.93

332883-48-4
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939-82-2
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Yield:939-82-2 96%

Reaction Conditions:

with N-Bromosuccinimide;triphenylphosphine in dichloromethane at 0; for 1.5 h;Inert atmosphere;

Steps:

53.2 1-Bromo-2-(bromomethyl)-4-nitrobenzene

Step 2
1-Bromo-2-(bromomethyl)-4-nitrobenzene
To a stirred solution of (2-bromo-5-nitrophenyl)methanol (9 g, 38.7 mmol), PPh₃ (15.2 g, 58.18 mmol) in dry dichloromethane (100 mL), NBS (13.8 g, 77.58 mmol) was added in portions at 0° C. under argon atmosphere.
The reaction mixture was stirred for 1.5 h at 0° C.
The reaction mixture was diluted with dichloromethane (100 mL), washed with water, brine, dried over Na₂SO₄ and concentrated.
The crude product was purified on a silica gel column, eluting with ethyl acetate in pet-ether (3:97) to afford 1-bromo-2-(bromomethyl)-4-nitrobenzene (11 g, 96%, LC-MS 92.9%) as an off-white solid. ¹H NMR (400 MHz, CDCl₃), δ 8.33 (d, J=2.4 Hz 1H), 8.03 (dd, J=8.8, 3.2 Hz, 1H), 7.78 (d, J=8.8 Hz 1H), 4.63 (s, 2H).

References:

US2017/369489,2017,A1 Location in patent:Paragraph 0513; 0515

7149-70-4 Synthesis