Triphosgene → 6-Bromo-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 44190

Reaction equation

HRID 44190 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][OH:10].Cl[C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:12](=[O:14])[O:10][CH2:9][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 110308742-Amino-5-bromobenzenemethanol

Product 1

HCID 259189636-Bromo-1,4-dihydro-2H-3,1-benzoxazin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-amino-5-bromophenyl)methanol (772 mg, 3.8 mmol) in 15 ml THF was added triphosgene (1.03 g, 3.8 mmol) under nitrogen. After precipitation of a colorless solid, stirring was continued for 20 min before water was added. The solution was extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated, affording 6-bromo-1H-benzo[d][1,3]oxazin-2(4H)-one (830 mg, 3.64 mmol, 96%) as colorless solid.

Workup

  1. customAfter precipitation of a colorless solid
  2. additionwas added
  3. extractionThe solution was extracted several times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-832a93207d004a2982842647434dcf26
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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