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

HRID 622716Notes

Reaction equation

HRID 622716 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 1 N 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 (2 H, 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-25ac834d0ca8400b8ccfa351990afcbc
Source dataset
uspto-grants-1988_09
Patent number
US04772626

Reaction notes

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