Methyl 2-fluoro-4-nitrobenzoate → (2-Fluoro-4-nitrophenyl)methanol

HRID 1843043Notes

Reaction equation

HRID 1843043 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 3013872Methyl 2-fluoro-4-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 17981733(2-Fluoro-4-nitrophenyl)methanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-fluoro-4-nitrobenzoate (10.0 g, 49.7 mmol, 1 eq.) in methanol (100 mL) was added sodium borohydride (9.40 g, 248.7 mmol, 5 eq.) at RT and stirred for 4 h. The methanol was evaporated and the residue was diluted with ethyl acetate (50 mL×2) washed with water (50 mL) and brine (50 mL). The ethyl acetate layer was dried over Na2SO4, evaporated under vacuum to get (2-fluoro-4-nitrophenyl)methanol (8 g, 94%, off-white solid; TLC system: EtOAc/PE (3:7), Rf: 0.30).

Workup

  1. customThe methanol was evaporated
  2. additionthe residue was diluted with ethyl acetate (50 mL×2)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialThe ethyl acetate layer was dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-8ee785a2b5d64ed1a8e5735280bd8990
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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