Hydrochloric Acid → 3-(Hydroxymethyl)-5-(trifluoromethoxy)benzonitrile

HRID 2040515Notes

Reaction equation

HRID 2040515 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[BH4-].[Na+].CO.Cl>C1COCC1>[OH:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:11]=[C:10]([O:12][C:13]([F:14])([F:15])[F:16])[CH:9]=1)[C:1]#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 866469923-Cyano-5-(trifluoromethoxy)benzoyl chloride

Product 1

HCID 668475343-(Hydroxymethyl)-5-(trifluoromethoxy)benzonitrileYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyano-5-(trifluoromethoxy)benzoyl chloride (844 mg, 3.38 mmol) was dissolved in THF (10 mL) and cooled to 0° C. Sodium borohydride (320 mg, 8.45 mmol) was added, followed by methanol (2 mL) and the reaction was stirred for 20 min at 0° C. before it was allowed to warm to room temperature. After 2 h, the reaction mixture was acidified to pH 3 with 1.0 M HCl. The aqueous mixture was extracted with ethyl acetate and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (440 mg). LCMS m/z=218.3 [M+H]+.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 2 h
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d9714006805436ba1b6e6a4a9480e66
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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