4-Chloro-3-fluorobenzyl Bromide synthesis
- Product Name:4-Chloro-3-fluorobenzyl Bromide
- CAS Number:206362-80-3
- Molecular formula:C7H5BrClF
- Molecular Weight:223.47
202925-10-8
206362-80-3
Step 1: Bromine (16.5 g, 0.103 mol) was added dropwise to a solution of triphenylphosphine (27.8 g, 0.103 mol) in dichloromethane (200 mL) at 0°C while stirring. After the dropwise addition was completed, stirring of the reaction mixture was continued for 10 minutes. Subsequently, 4-chloro-3-fluorobenzyl alcohol (15.8 g, 0.098 mol) was added and the reaction mixture was stirred for 30 minutes. Upon completion of the reaction, the reaction was quenched with ethanol and the mixture was poured into saturated sodium bicarbonate solution and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. Purification by silica gel column chromatography afforded 4-(bromomethyl)-1-chloro-2-fluorobenzene (18.6 g, 85% yield).1H-NMR (400 MHz, CDCl3): δ = 7.27 (t, J = 7.9 Hz, 1H), 7.10 (dd, J = 7.9 Hz, 2.1 Hz, 1H), 7.04-6.99 (m, 1H). 4.32 (s, 2H).
202925-10-8
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206362-80-3
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Yield: 85%
Reaction Conditions:
with bromine;triphenylphosphine in ethanol;dichloromethane at 0; for 0.5 h;
Steps:
Step 1:
4-(bromomethyl)-1-chloro-2-fluorobenzene
Step 1:
4-(bromomethyl)-1-chloro-2-fluorobenzene
,To a solution of triphenylphosphine (27.8 g, 0.103 mol) in CH2Cl2 (200 mL), bromine (16.5 g, 0.103 mol) was added dropwise at 0°C under stirring.
Upon completion of the addition, the resultant was stirred for 10 minutes. (4-Chloro-3-fluorophenyl)methanol (15.8 g, 0.098mol) was then added.
The resultnat was stirred for 30 minutes.
The reaction was quenched with ethanol, poured into saturated sodium bicarbonate solution, and extracted with CH2Cl2.
The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to give 4-(bromomethyl)-1-chloro-2-fluorobenzene (18.6 g, 85% yield).
1H-NMR (400 MHz, CDCl3):δ= 7.27 (t, J = 7.9Hz, 1H), 7.10 (dd, J= 7.9 Hz, 2.1 Hz, 1H), 7.04-6.99 (m, 1H), 4.32 (s, 2H).
References:
Chia Tai Tianqing Pharmaceutical Group Co.,Ltd;Centaurus BioPharma Co., Ltd.;Lianyungang Runzhong Pharmaceutical Co., Ltd.;XIAO, Dengming;XU, Xinhe;LIU, Xijie;HU, Yuandong;YU, Honghao;LIU, Zhihua;PENG, Yong;SUN, Yinghui;LUO, Hong;KONG, Fansheng;HAN, Yongxin;SUN, Jian EP2952510, 2015, A1 Location in patent:Paragraph 0185
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206362-80-3
132 suppliers
$9.00/1g