Water → HCID 66652771, compound

HRID 2167889Notes

Reaction equation

HRID 2167889 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-4fb00f349b1e45e7ba4d86866a8720a8
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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