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

HRID 413163Notes

Reaction equation

HRID 413163 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 68822414HCID 68822414, compound

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 stirred 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-2c8c688bdb1746a4b47c814071d89545
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

Loading…