Sodium borohydride → (3-Bromo-6-chloro-2-fluorophenyl)methanol

HRID 2249371Notes

Reaction equation

HRID 2249371 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([Cl:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>C(O)C.O>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH2:5][OH:6])[C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 592994573-Bromo-6-chloro-2-fluorobenzaldehyde

Product 1

HCID 59299314(3-Bromo-6-chloro-2-fluorophenyl)methanolYield 51.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (20.0 g, 0.084 mol) in ethanol (250 mL) was added sodium borohydride (6.4 g, 0.168 mol) and the reaction mixture was stirred at ambient temperature for 1 hour. The mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×200 mL), dried (sodium sulfate) and concentrated. The crude solid was recrystallized from hexanes to give (3-bromo-6-chloro-2-fluorophenyl) methanol (10.4 g, 0.043 mol): 1H NMR (CDCl3): δ 7.50 (m, 1H), 7.15 (dt, 1H), 4.90 (s, 2H), 2.10 (bs, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe crude solid was recrystallized from hexanes

Sources & evidence

ORD record
ord-8f56741abe8643ef9b14b06138ae126e
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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