Hydrochloric Acid → 1-(4-Bromophenyl)-2,2,2-trifluoroethanol

HRID 1180448Notes

Reaction equation

HRID 1180448 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:11])([F:12])[F:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6038664'-Bromo-2,2,2-trifluoroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 112190241-(4-Bromophenyl)-2,2,2-trifluoroethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-bromophenyl)-2,2,2-trifluoroethanone (37.7 mmol, 8.86 g) in methanol (89 mL) at 0° C., was added sodium borohydride (39.6, 1.50 g). The mixture was stirred for 1 h. HCl 10% (100 mL) was added and the mixture was stirred for 0.25 h. The mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude alcohol was used without further purification.

Workup

  1. stirringthe mixture was stirred for 0.25 h
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude alcohol was used without further purification

Sources & evidence

ORD record
ord-1817108093134e2aaff9a4aaf4f5daea
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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