تفاعل #2075717

ord-420e9770288c42f790f133b1501725d9

معادلة التفاعل

[BH4-].[Na+]
Sodium borohydride
CC(=O)c1cc(Br)ccc1Cl
1-(5-bromo-2-chlorophenyl)ethanone
CC(O)c1cc(Br)ccc1Cl
title compound
المردود 99.3%
CC(O)c1cc(Br)ccc1Cl
1-(5-Bromo-2-chlorophenyl)-ethanol
المردود 99.3%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe resulting bubbling white mixture
  2. 2
    أخرىThe reaction mixture was quenched with acetone (50 mL)
  3. 3
    تركيزconcentrated by rotary evaporation
  4. 4
    أخرىThe residue was partitioned between ethyl acetate and water
  5. 5
    أخرىThe organic phase was dried
  6. 6
    تركيزconcentrated

الإجراء التجريبي

Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanone (10 g, 42.8 mmol) in methanol at 0° C., The resulting bubbling white mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 42.5 mmol, 99% yield) as a white solid: 1H NMR (CDCl3): δ 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07642220B2uspto-grants-2010_01