Sodium borohydride → HCID 67115831, compound

HRID 1258857Notes

Reaction equation

HRID 1258857 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][N:10](C(=O)C(F)(F)F)[C:9]=2[CH:20]=1.[BH4-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][NH:10][C:9]=2[CH:20]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866551991-[6-(2-Bromo-5-iodo-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 67115831HCID 67115831, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-[6-(2-bromo-5-iodo-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (12.0 g, 22.81 mmol) in methanol (100 mL) and THF (20 mL) was added sodium borohydride (1.73 g, 45.62 mmol) portion wise and the reaction mixture was stirred at room temperature for 1 h. The excess of sodium borohydride was quenched by adding 1N HCl. Methanol was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was washed with water, and brine, then concentrated to furnish the crude product which was purified by silica gel column chromatography to provide 6-(2-bromo-5-iodo-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (9.45 g).

Workup

  1. customThe excess of sodium borohydride was quenched
  2. additionby adding 1N HCl
  3. customMethanol was evaporated
  4. customthe residue was partitioned between dichloromethane and water
  5. washThe organic layer was washed with water, and brine
  6. concentrationconcentrated
  7. customto furnish the crude product which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e05e8ad90eb5421b9d5a08913a931d44
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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