Methanol → (2-Bromo-5-chlorophenyl)methanol

HRID 1081885Notes

Reaction equation

HRID 1081885 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=[O:5].CO.[BH4-].[Na+]>CC(C)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 153912792-Bromo-5-chlorobenzaldehyde

Product 1

HCID 23363134(2-Bromo-5-chlorophenyl)methanolYield 94.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromo-5-chlorobenzaldehyde (20.5 g) from Example 72 was dissolved with dry methanol (200 ml), followed by sodium borohydride (1.06 g) at 0° C., and the mixture was stirred for 30 minutes. After addition of acetone, the solvent was removed under reduced pressure, water was added the obtained residue, and then extracted with ether. The organic layer was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, to give the title compound (19.5 g; 94%)

Workup

  1. customthe solvent was removed under reduced pressure, water
  2. additionwas added the obtained residue
  3. extractionextracted with ether
  4. washThe organic layer was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a809ee0304c45d78f9ad7fea53648a1
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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