Hydrochloric Acid → 2-(4-Bromophenyl)-1,1,1-trifluoropropan-2-ol

HRID 2217283Notes

Reaction equation

HRID 2217283 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.[CH3:14][Mg]Br.Cl>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])([CH3:14])[C:9]([F:11])([F:12])[F:10])=[CH:4][CH:3]=1

Participants

5

Procedure

Commercial 1-(4-bromophenyl)-2,2,2-trifluoroethanone (1 g, 4 mmoles) in diethyl ether (8 mL) was cooled to −78° C. for the addition of commercial methylmagnesium bromide (2.65 mL, 7.9 mmoles, 3 M in diethyl ether). The cloudy reaction media was allowed to reach room temperature and stirred overnight. The reaction mixture was transferred to a separatory funnel containing 1.2 M hydrochloric acid (20 mL). This aqueous layer was extracted 3 times with ethyl acetate (30 mL). The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The clear oil was pure enough to be used without further purification.

Workup

  1. customThe cloudy reaction media
  2. customto reach room temperature
  3. customThe reaction mixture was transferred to a separatory funnel
  4. extractionThis aqueous layer was extracted 3 times with ethyl acetate (30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto be used without further purification

Sources & evidence

ORD record
ord-4abc8ecae4874cec9af756b8ee61da4a
Source dataset
uspto-grants-2008_08
Patent number
US07407959B2

Reaction notes

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