Sodium borohydride → 3-(6-Bromo-2-fluoro-3-hydroxymethyl-phenoxy)-5-chloro-benzonitrile

HRID 2234855Notes

Reaction equation

HRID 2234855 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])=[C:8]([F:20])[C:7]([CH:21]=[O:22])=[CH:6][CH:5]=1>C1COCC1.CO>[Br:3][C:4]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])=[C:8]([F:20])[C:7]([CH2:21][OH:22])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866184923-(6-Bromo-2-fluoro-3-formyl-phenoxy)-5-chloro-benzonitrile

Product 1

HCID 669992083-(6-Bromo-2-fluoro-3-hydroxymethyl-phenoxy)-5-chloro-benzonitrileYield 47.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (0.64 g, 1.5 equiv) was added portionwise to a stirred solution of 105 (4.0 g, 11.3 mmol) in a mixture of THF (20 mL) and MeOH (10 mL) at RT. The reaction mixture was stirred for 12 h, and quenched by the addition of saturated aqueous NH4Cl. The aqueous mixture was extracted with EtOAc, and the organic solution was washed with water and evaporated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (20% to 50% EtOAc) to afford 1.9 g (47%) of 3-(6-bromo-2-fluoro-3-hydroxymethyl-phenoxy)-5-chloro-benzonitrile (107) as a yellow oil.

Workup

  1. customquenched by the addition of saturated aqueous NH4Cl
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washthe organic solution was washed with water
  4. customevaporated
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with an EtOAc/hexane gradient (20% to 50% EtOAc)

Sources & evidence

ORD record
ord-d40e6c3159c849578178353b0706e7da
Source dataset
uspto-grants-2010_05
Patent number
US07713974B2

Reaction notes

Loading…