Bromine → 2-Bromo-1-[8-(tert-butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

HRID 249719Notes

Reaction equation

HRID 249719 reaction equation
[C:1]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]=2[CH:8]=[C:7]([C:16](=[O:18])[CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]Br>C(O)(=O)C.C1(C)C=CC=CC=1>[Br:19][CH2:17][C:16]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:14]2[O:13][CH2:12][CH2:11][N:10]([CH3:15])[C:9]=2[CH:8]=1)=[O:18]

Participants

5

Reactant 2

HCID 24408BromineHCID 589100321-[8-(tert-Butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

Product 1

HCID 589099482-Bromo-1-[8-(tert-butyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanoneYield 13%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

1-(8-tert-Butyl-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)ethanone (250 mg, purchased from Chembiotek, India) was warmed to 50° C. to 55° C. in a mixture of acetic acid (4 ml) and toluene (8 ml). Bromine (200 mg dissolved in acetic acid) was carefully added dropwise at this temperature. After 2.5 h, the heating was removed, and the mixture was treated with ice water at RT and extracted three times with toluene. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified on silica gel, so that 65 mg of the desired compound were obtained, in addition to a further 43 mg of product, which were slightly contaminated, and 37 mg of starting material.

Workup

  1. customthe heating was removed
  2. additionthe mixture was treated with ice water at RT
  3. extractionextracted three times with toluene
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on silica gel, so that 65 mg of the desired compound

Sources & evidence

ORD record
ord-f2e4196a1a78498c8d481a8fa0b71c24
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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