Bromine → 6-Bromo-5-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 635806Notes

Reaction equation

HRID 635806 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][O:9][C:8](=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]Br>C(O)(=O)C.C(O)(C(F)(F)F)=O>[Br:13][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8](=[O:12])[O:9][CH2:10][C:11]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 105589525-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Product 1

HCID 107765166-Bromo-5-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-methyl-1,4-dihydro-benzo[d] [1,3]oxazin-2-one (0.695 g, 4.3 mmol) in acetic acid (5 mL), Br2 (0.805 g=5 mmol) solution in TFA (5 mL)+acetic acid (5 mL) was added at 10° C. Reaction mixture was stirred for 2 hours and poured over ice water. Yellow precipitate was filtered and dried at 120° C.

Workup

  1. customReaction mixture
  2. filtrationYellow precipitate was filtered
  3. customdried at 120° C.

Sources & evidence

ORD record
ord-1631c6ae0a814f90a62a783f6a1b5dec
Source dataset
uspto-grants-2001_02
Patent number
US06191134B1

Reaction notes

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