Sodium borohydride → HCID 67115789, compound

HRID 72573Notes

Reaction equation

HRID 72573 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 (1.5 g, 39.0 mmol) portion wise and the reaction mixture was stirred overnight. Excess of NaBH4 was quenched by adding aq. NH4Cl, and ethanol was evaporated. The residue was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine (40 mL) and dried over sodium sulphate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (6.1 g).

Workup

  1. customExcess of NaBH4 was quenched
  2. additionby adding aq. NH4Cl, and ethanol
  3. customwas evaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. washwashed with brine (40 mL)
  7. dry with materialdried over sodium sulphate
  8. customCrude product obtained
  9. customafter evaporation of solvent
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-27b0ff796a2f4763b30295d720fd1d9c
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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