Sodium borohydride → 2-(2,2,2-Trifluoroethyl)phenol

HRID 858678Notes

Reaction equation

HRID 858678 reaction equation
[BH4-].[Na+].Cl[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:5]([F:8])([F:7])[F:6]>C1COCC1>[F:6][C:5]([F:7])([F:8])[CH2:4][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15]

Participants

4

Procedure

Sodium Borohydride (0.930 g) was added to a solution of 2-(1-chloro-2,2,2-trifluoroethyl)phenol (2.6 g) in THF (30 ml). The reaction mixture was then stirred for 14 hrs at room temperature under an atmosphere of nitrogen, after which time the reaction was quenched with 1N HCl (50 ml) and partitioned between 1NHCl (100) and ethyl acetate (200 ml), the organics were separated and dried over magnesium sulfate, filtered and solvent evaporated in vacuuo to afford title compound as a semi solid (2.4 g). 1H NMR (CDCl3): δ 3.50 (q, J=21.06 Hz 2H), 6.80 (m, 1H), 7.00 (m, 1H), 7.25 (m, 2H).

Workup

  1. customafter which time the reaction was quenched with 1N HCl (50 ml)
  2. custompartitioned between 1NHCl (100) and ethyl acetate (200 ml)
  3. customthe organics were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated in vacuuo

Sources & evidence

ORD record
ord-018faa6cf3f2483091bab98a7c3e5872
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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