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

HRID 1725053Notes

Reaction equation

HRID 1725053 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-cbc80a00db1f4743874f09ffb157e940
Source dataset
uspto-grants-2009_02
Patent number
US07488822B2

Reaction notes

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