Bromine → 7-bromo-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 885932Notes

Reaction equation

HRID 885932 reaction equation
[CH3:1][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>C(Cl)Cl.C1COCC1>[Br:13][C:3]1[C:2]([CH3:1])=[CH:12][C:6]2[NH:7][C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 27638392H-1,4-Benzoxazine-3(4H)-one, 6-methyl-

Product 1

HCID 671865677-bromo-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 80.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-methyl-2H-1,4-benzoxazin-3(4H)-one (10.0 g, 61.3 mmol) in DCM (200 mL) and THF (200 mL) at 0° C. was added bromine (15.0 g, 93.7 mmol) dropwise. The reaction mixture was stirred at this temperature for 30 minutes, then filtered. The solid was washed with Et2O (200 mL) to give the title compound (11.95 g, 80%) as a white solid that was used without further purification. δH (CDCl3) 8.95 (1H, s), 7.16 (1H, s), 6.70 (1H, s), 4.59 (2H, s), 2.31 (3H, s).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with Et2O (200 mL)

Sources & evidence

ORD record
ord-ea0e1079e26d4915a0a11a58afcdb3f1
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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