Methanol → 2-(3-Fluorophenyl)ethanol

HRID 368819Notes

Reaction equation

HRID 368819 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1.CO>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 676173-Fluorophenylacetic acid

Product 1

HCID 5731322-(3-Fluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide complex (9.15 ml, 96.5 mmol) is added dropwise and then faster as gas evolution slowed, to an ice-cooled mixture of 3-fluorophenyl acetic acid (XXXIX, 4.96 g, 32.2 mmol) in THF (30 ml). After 2 hr methanol is added dropwise over the course of several hours. The solvents are then removed under reduced pressure and methanol is again added and removed under reduced pressure. The methanol addition/removal is repeated three times and then the residue is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated to give 2-(3-fluorophenyl)ethanol (LXV), MS (m/z) 140; IR (neat) 1590, 1046, 1450, 1141, 782, 1488 and 691 cm-1.

Workup

  1. additionBorane-dimethyl sulfide complex (9.15 ml, 96.5 mmol) is added dropwise
  2. temperaturecooled
  3. customThe solvents are then removed under reduced pressure and methanol
  4. additionis again added
  5. customremoved under reduced pressure
  6. customThe methanol addition/removal
  7. customthe residue is partitioned between dichloromethane and aqueous sodium bicarbonate
  8. dry with materialThe organic layers are dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8ed2c7737c1d4c03a8b50a01f07ccb38
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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