Methanol → 2-(2-Fluoro-5-nitrophenyl)ethanol

HRID 64344Notes

Reaction equation

HRID 64344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:12](O)=[O:13].CO>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 8493592-Fluoro-5-nitrophenylacetic acid

Product 1

HCID 248284032-(2-Fluoro-5-nitrophenyl)ethanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2-fluoro-5-nitrophenyl)acetic acid (2.0 g, 10 mmol) in THF (50 mL) was added borane dimethyl sulfide complex solution (4.0 g, 25 mmol). The reaction was warmed to 60° C. stirred for about 12 hr. After cooling down to RT, CH3OH (20 mL) was slowly added to the reaction, concentrated under reduced pressure to remove solvent. The residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1) to afford the product as a colorless oil (1.6 g, 86.1%). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (t, J=3.2, 6.4 Hz, 1 H), 8.19-8.14 (m, 1 H), 8.45 (t, J=9.2 Hz, 1 H), 4.80 (t, J=5.6 Hz, 1 H), 3.66 (dt, J=5.6, 6.4 Hz, 1 H), 2.86 (t, J=6.4 Hz, 2 H). MS (ESI) m/e [M+1]+ 186.

Workup

  1. temperatureAfter cooling down to RT
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. customThe residue was purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1)

Sources & evidence

ORD record
ord-6531ebd2a299490dbb8aedcb697991e7
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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