Ethanol → (5-Bromo-2-fluorophenyl)methanol

HRID 1722321Notes

Reaction equation

HRID 1722321 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[F:13])(=O)C.CCO.[OH-].[Na+].O>CCOCC>[Br:12][C:10]1[CH:9]=[CH:8][C:7]([F:13])=[C:6]([CH:11]=1)[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 13553296HCID 13553296, compound

Product 1

HCID 2773352(5-Bromo-2-fluorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the compound (1b) (3.2 g, 14.5 mmol), EtOH (20 mL) and 1N NaOH (20 mL, 20 mmol) was stirred at reflux under N2 for 1.5 hours. The reaction mixture was cooled and distributed between H2O (150 mL) and Et2O (150 mL). The organic layer was separated and washed with H2O (2×100 mL), dried and the clear faint yellow solution was evaporated. Distillation of the residue provided the compound (1c) as a clear colorless oil; bp 82°-87° C. (0.4 mm); NMR 3.3 (H, br s), 4.6 (2H, s), 6.81 (H3, t, J=9 Hz), 7.15-7.37 (H4, m), 7.44 (H6, dd, J=3 and 6 Hz).

Workup

  1. temperatureat reflux under N2 for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. washwashed with H2O (2×100 mL)
  5. customdried
  6. customthe clear faint yellow solution was evaporated
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-b6d907dd2331466195a8798f0c07004a
Source dataset
uspto-grants-1989_08
Patent number
US04855321

Reaction notes

Loading…