3-Nitro-5-(trifluoromethyl)benzoic acid → (3-Nitro-5-(trifluoromethyl)phenyl)methanol

HRID 1640129Notes

Reaction equation

HRID 1640129 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (52.2 g, 0.222 mol) in THF (370 mL) at 0° C. was added BH3 (1M in THF, 444 mL) slowly. The reaction mixture was allowed to stir and warm to rt. After 30 min, the reaction was quenched by the addition of sat. aq. NaHCO3 at 0° C. and extracted with Et2O. The organic solutions were combined, washed with brine, dried over MGSO4, filtered and concentrated. The crude material (45.8 g, 93%) was used in the next step without purification.

Workup

  1. customthe reaction was quenched by the addition of sat. aq. NaHCO3 at 0° C.
  2. extractionextracted with Et2O
  3. washwashed with brine
  4. customdried over MGSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material (45.8 g, 93%) was used in the next step without purification

Sources & evidence

ORD record
ord-01bc305e643742bb9c7f8fc2a7685794
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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