Hydrochloric Acid → 2,3-Difluoro-α-methyl-6-nitrobenzeneethanol

HRID 1656750Notes

Reaction equation

HRID 1656750 reaction equation
[F:1][C:2]1[C:3]([CH2:12][C:13](=[O:15])[CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].Cl>CO>[F:1][C:2]1[C:3]([CH2:12][CH:13]([OH:15])[CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 142688761-(2,3-Difluoro-6-nitrophenyl)propan-2-one

Product 1

HCID 142688772,3-Difluoro-α-methyl-6-nitrobenzeneethanolYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31.2 g (145 mmol) of the compound (148) obtained above was added to 500 ml of methanol, and while cooling on ice, 6.04 g (160 mmol) of sodium borohydride was added to the solution through 5 minutes. After the solution was stirred for 30 minutes as was, the solution was stirred overnight at room temperature. 100 ml of 4N hydrochloric acid was added slowly to the solution and the solution was stirred for 30 minutes at room temperature. Then, the solvent was removed by distillation. The solution was extracted with 400 ml of chloroform, and after drying over magnesium sulfate, the solvent was removed by distillation to obtain 27.7 g of the subject compound (149) in a 89% yield.

Workup

  1. additionwas added to the solution through 5 minutes
  2. stirringthe solution was stirred overnight at room temperature
  3. stirringthe solution was stirred for 30 minutes at room temperature
  4. customThen, the solvent was removed by distillation
  5. extractionThe solution was extracted with 400 ml of chloroform
  6. dry with materialafter drying over magnesium sulfate
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-66a3b73e3eaf46fe9e76d4bed7d1f229
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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