Bromine → HCID 22138576, compound

HRID 1825709Notes

Reaction equation

HRID 1825709 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[Br:13]Br>ClCCl>[Br:13][C:3]1[C:2]([F:1])=[CH:12][C:6]2[NH:7][C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 3028976-Fluoro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 22138576HCID 22138576, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

30.0 g of 6-fluoro-4H-benz[1,4]oxazin-3-one are initially charged in 300 ml of dichloromethane, and 37.4 g of bromine are then slowly added dropwise at room temperature. The mixture is heated at 30° C. with stirring for 15 h. The reaction solution is cooled to room temperature and poured onto ice. The aqueous phase is extracted repeatedly with dichloromethane. The combined organic phases are washed with saturated sodium thiosulphate solution, dried over magnesium sulphate and concentrated. This give 44.1 g (yield 99.5% of theory) of 7-bromo-6-fluoro-4H-benz[1,4]oxazin-3-one of melting point 244° C.

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. additionpoured onto ice
  3. extractionThe aqueous phase is extracted repeatedly with dichloromethane
  4. washThe combined organic phases are washed with saturated sodium thiosulphate solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d54922b15aaf4c84aa8855855ac04a89
Source dataset
uspto-grants-2006_05
Patent number
US07049271B2

Reaction notes

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