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

HRID 1453129Notes

Reaction equation

HRID 1453129 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

Reactant 2

HCID 4311764Sodium borohydrideHCID 587627412-(1-Chloro-2,2,2-trifluoroethyl)phenol

Product 1

HCID 177969212-(2,2,2-Trifluoroethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 1N HCl (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 1N HCl (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-3da85c5c8f8a411c867b07ebd2be150a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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