Sodium borohydride → HCID 67115789, compound

HRID 72567Notes

Reaction equation

HRID 72567 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[C:12]=2[CH:23]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 583408561-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 67115789HCID 67115789, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (8.6 g, 19.8 mmol) in ethanol (40 mL) was added NaBH4 portion wise and the reaction mixture was stirred overnight. The excess of NaBH4 was quenched by adding aq. HCl. Ethanol was evaporated and the residue was partitioned between dichloromethane and water. Organic layer was washed with brine, water, dried over sodium sulfate followed by evaporation of solvent furnished 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (6.1 g).

Workup

  1. customThe excess of NaBH4 was quenched
  2. additionby adding aq. HCl
  3. customEthanol was evaporated
  4. customthe residue was partitioned between dichloromethane and water
  5. washOrganic layer was washed with brine, water
  6. dry with materialdried over sodium sulfate
  7. customfollowed by evaporation of solvent

Sources & evidence

ORD record
ord-b047f4e6a36947998d827108c4b7083d
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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