Water → HCID 66652771, compound

HRID 920572Notes

Reaction equation

HRID 920572 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]([F:13])[F:12])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:11]([F:13])[F:12])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 51888875HCID 51888875, compound

Product 1

HCID 66652771HCID 66652771, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-6-difluoromethoxy-benzaldehyde (0.65 g; 3.15 mmol) in MeOH (10 mL) was added NaBH4 (357.13 mg; 9.44 mmol), at −15° C. After complete addition the mixture was allowed to warm to RT and stirred for 30 minutes. Subsequently, water (5 mL) was added and the volatiles were removed in vacuo. The residue was partitioned between Et2O and 5% aqueous NaHCO3. The layers were separated and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford (2-chloro-6-difluoromethoxy-phenyl)-methanol (0.52 g), which was used as such.

Workup

  1. customat −15° C
  2. additionAfter complete addition the mixture
  3. customthe volatiles were removed in vacuo
  4. customThe residue was partitioned between Et2O and 5% aqueous NaHCO3
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17754eabf1224c69bc9c1cdb1deb874f
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…