Bromine → 6-Bromo-8-fluoro-4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1882829Notes

Reaction equation

HRID 1882829 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH2:5][CH:6]2[C:11]([CH3:13])([CH3:12])[O:10][C:9](=[O:14])[NH:8][C:7]=12.[Br:15]Br>C(O)(=O)C>[Br:15][C:4]1[CH2:5][CH:6]2[C:11]([CH3:12])([CH3:13])[O:10][C:9](=[O:14])[NH:8][C:7]2=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 688224148-Fluoro-4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 688225046-Bromo-8-fluoro-4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 8-fluoro-4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one (0.15 g, 0.77 mmol) in acetic acid (5 mL) was added dropwise a solution of bromine (0.37 g, 2.31 mmol) in acetic acid (5 mL) under nitrogen at rt. After stirring for 10 minutes, the mixture was concentrated and the residue obtained was purified by a silica gel column (hexane:ethyl acetate/4:1) to afford 6-bromo-8-fluoro-4,4-dimethyl-dihydro-benzo[d][1,3]oxazin-2-one as an off-white solid (0.176 g, 84%) which was used in next step without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue obtained
  3. customwas purified by a silica gel column (hexane:ethyl acetate/4:1)

Sources & evidence

ORD record
ord-f27c606c6b2d4a1bb80dca4972a53188
Source dataset
uspto-grants-2004_07
Patent number
US06759408B2

Reaction notes

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