Triphosgene → 5-Bromo-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 459798Notes

Reaction equation

HRID 459798 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9][OH:10].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Br:8][C:4]1[C:3]2[CH2:9][O:10][C:12](=[O:14])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 184444672-Amino-6-bromobenzenemethanol

Product 1

HCID 184445205-Bromo-1H-benzo[d][1,3]oxazin-2(4H)-oneYield 268.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-Amino-6-bromo-phenyl)-methanol (549 mg, 2.72 mmol) and triphosgen (282 mg, 0.95 mmol) in THF (20 ml) was heated at 50° C. for an hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed by water and brine. After drying over MgSO4, the solution was concentrated under vacuum to give 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (582 mg, 94%) as a white solid. MS: 226.1 (M−H)−. (M+H)−.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed by water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-2c06167387b64c15aaf3ee646d30489a
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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