Sodium borohydride → 2-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)benzonitrile

HRID 536150Notes

Reaction equation

HRID 536150 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666201Benzonitrile, 2-[4-chloro-3-(trifluoromethyl)phenoxy]-5-formyl-

Product 1

HCID 668256082-(4-Chloro-3-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)benzonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-formylbenzonitrile (5.0 g, 15.4 mmol) in methanol (50 mL) was added sodium borohydride (0.61 g, 16.1 mmol) at 0° C. The reaction mixture was stirred at rt for 30 min and concentrated. Purification via ISCO system (CH2Cl2/MeOH-20/1) afforded the title product (4.76 g) as an off-white solid. LC-MS (ESI): m/z 328 [M+H]+; 3.96 min (ret time).

Workup

  1. concentrationconcentrated
  2. customPurification via ISCO system (CH2Cl2/MeOH-20/1)

Sources & evidence

ORD record
ord-406ebfa6459e48fcaabd59c0456cd3a8
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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