Sodium borohydride → 2',6-Dichloro-4-ethyl-[1,1'-biphenyl]-3-amine

HRID 588805Notes

Reaction equation

HRID 588805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([CH:15]=[CH2:16])=[C:10]([NH2:17])[CH:9]=1.[BH4-].[Na+]>CO.Cl[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([CH2:15][CH3:16])=[C:10]([NH2:17])[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 904603862',6-Dichloro-4-vinyl-[1,1'-biphenyl]-3-amine

Product 1

HCID 904625672',6-Dichloro-4-ethyl-[1,1'-biphenyl]-3-amineYield 59.4%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2′,6-dichloro-4-vinyl-[1,1′-biphenyl]-3-amine (500 mg, 1.9 mmol), CuCl (225 mg, 2.28 mmol) in MeOH (10 mL) at 0° C., NaBH4 (722 mg, 19 mmol) was added in portions and the resulting mixture was stirred at room temperature for 20 min. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1) to afford the desired product (300 mg, 59.4% yield). ESI-MS m/z: 266.0[M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-84a01c8671a245809dca9c8cb91b8a6d
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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