Hydrochloric Acid → 1-(2-Chloro-6-fluorophenyl)ethan-1-ol

HRID 1903834Notes

Reaction equation

HRID 1903834 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[F:11])=[O:3].[BH4-].[Na+].[OH-].[Na+].Cl>C(O)(C)C.O>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([F:11])[C:4]=1[CH:2]([OH:3])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27735781-(2-Chloro-6-fluorophenyl)ethan-1-one2×HCID 4311764Sodium borohydride

Product 1

HCID 133042791-(2-Chloro-6-fluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

2-chloro-6-fluoroacetophenone of (A) (45.0 g, 0.26 mol) is dissolved in isopropyl alcohol (98 ml) and NaBH4 (4.9 g, 0.13 mol) is added. The resultant mixture is warmed to 55° C. for about 16 hours. A solution of NaOH 10.4 g, 0.26 mol) in water (41. ml) is then added. After 1 hour at 55° C., this reaction mixture is cooled and acidified with diluted HCl. Extraction with chloroform provided pure title product (45.1 g, 99.1%).

Workup

  1. temperaturethis reaction mixture is cooled
  2. extractionExtraction with chloroform provided pure title product (45.1 g, 99.1%)

Sources & evidence

ORD record
ord-1b8f09cf9d514dc2a73735722d863125
Source dataset
uspto-grants-1984_03
Patent number
US04438271

Reaction notes

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