5-Chloro-2-fluorobenzyl bromide synthesis
- Product Name:5-Chloro-2-fluorobenzyl bromide
- CAS Number:71916-91-1
- Molecular formula:C7H5BrClF
- Molecular Weight:223.47
452-66-4
71916-91-1
General procedure for the synthesis of 5-chloro-2-fluorobenzyl bromide from 5-chloro-2-fluorotoluene: A: 5-Chloro-2-fluorotoluene (100 g, 692 mmol) was dissolved in ethyl acetate (300 ml) at 20 °C. To this solution N-bromosuccinimide (147.7 g, 830 mmol) and dibenzoyl peroxide (2 g, 8.25 mmol) were added sequentially. The reaction mixture was heated to 80 °C and stirred for 3 hours. Upon completion of the reaction, heptane (300 ml) was added and the mixture was cooled to 0 °C, at which time the succinimide precipitated. After filtration and washing with heptane, the residue was washed with water (1500 ml). The filtrate was concentrated to dryness under vacuum to give 162 g of the crude product 5-chloro-2-fluorobenzyl bromide. The crude product (141 g) was purified by vacuum distillation at 99 °C and 33 mbar to give the final 5-chloro-2-fluorobenzyl bromide (99 g, 75% yield). The purity of the product was analyzed by GC to be 87.1% (% area).1H-NMR (CDCl3) data: δ 4.44 (2H, d, CH2), 7.01 (1H, t, H3), 7.26 (1H, m, H4), 7.38 (1H, m, H6).
452-66-4
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71916-91-1
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Yield:71916-91-1 75%
Reaction Conditions:
with N-Bromosuccinimide;dibenzoyl peroxide in ethyl acetate at 20 - 80; for 3 h;
Steps:
6.A
A: 5-chloro-2-fluoro-benzylbromide5-Chloro-2-fluoro-toluene (100 g, 692 mmol) was dissolved in ethylactate (300 ml) at 20 0C. To this solution N-bromosuccinimide (147.7 g, 830 mmol) and dibenzoyl peroxide (2 g, 8.25 mmol) was added. The mixture was stirred at 80 0C for 3 hours.Heptane (300 ml) was added and the solution was cool to 0 °C whereupon
References:
N.V. ORGANON WO2008/3460, 2008, A1 Location in patent:Page/Page column 23-24