Sodium borohydride → (4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol

HRID 705847Notes

Reaction equation

HRID 705847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866661874-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 66825563(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)methanolYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzaldehyde (21 g, 69.8 mmol) in methanol (200 mL) was added slowly NaBH4 (2.64 g, 69.8 mmol) portionwise. The mixture was stirred at room temperature overnight. After removing the solvent, the residue diluted with DCM. The resulting suspension was filtered, the filtrate was concentrated in vacuo to afford the title compound (17.6 g, 55.2 mmol, 79% yield) as yellow solid. LCMS: rt=1.71 min, [M+H+]=303, 305

Workup

  1. customAfter removing the solvent
  2. additionthe residue diluted with DCM
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-43a00536b32b4ed990a1739f09c5afde
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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