3-Chloro-2-fluorobenzaldehyde → 3-Chloro-2-fluorobenzyl alcohol

HRID 2277575Notes

Reaction equation

HRID 2277575 reaction equation
[F:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C1COCC1.C(Cl)Cl>[Cl:10][C:9]1[C:2]([F:1])=[C:3]([CH2:4][OH:5])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 7363353-Chloro-2-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27736063-Chloro-2-fluorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-3-chloro-benzaldehyde (4.74 g, 30 mmol) in THF (20 mL) was added NaBH4 (1.48 g, 40 mmol). The resulting mixture was stirred at room temperature for 30 min before diluting with DCM. The organic layer was washed with water and brine. The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give desired product without further purification (4.8 g, 100%). MS: 161.0 (M+H)+.

Workup

  1. washThe organic layer was washed with water and brine
  2. customThe combined organic layers were dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eee0d38234e948a18495c89494babee2
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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