Sodium borohydride → HCID 59410050, compound

HRID 1915485Notes

Reaction equation

HRID 1915485 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([F:18])=[CH:11][C:10]=1[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[CH2:1]([O:8][C:9]1[C:10]([C:19]([F:22])([F:20])[F:21])=[CH:11][C:12]([F:18])=[C:13]([CH:14]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59410077HCID 59410077, compound

Product 1

HCID 59410050HCID 59410050, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(benzyloxy)-4-fluoro-5-nitro-2-(trifluoromethyl)benzene (382 mg, 1.21 mmol) and NiCl2 (314 mg, 2.42 mmol) in methanol (40 mL) was added NaBH4 (50 mg, 1.32 mmol) portionwise at 0° C. The reaction turned black after 20 minutes. The reaction mixture was quenched with NaHCO3 and diluted with EtOAc. The reaction mixture was then filtered through a plug of celite, the layers separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was then purified by silica gel column chromatography using 15% EtOAc/hexane gradient to give 5-(benzyloxy)-2-fluoro-4-(trifluoromethyl)aniline (150 mg, 43%). LC/MS: m/z 286.1 (M+H)+ at 1.89 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe reaction mixture was quenched with NaHCO3
  2. additiondiluted with EtOAc
  3. filtrationThe reaction mixture was then filtered through a plug of celite
  4. customthe layers separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-74dcd5281c1f4d01a334ac8031f7d33b
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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