Potassium Carbonate → 8-Bromo-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1270099노트

반응식

HRID 1270099 반응식
Br[C:2]([CH3:15])([CH3:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[C:7]=1[OH:13])=[O:4].C([O-])([O-])=O.[K+].[K+].O.C(OCC)(=O)C>CN(C=O)C>[Br:12][C:8]1[C:7]2[O:13][C:2]([CH3:15])([CH3:14])[C:3](=[O:4])[NH:5][C:6]=2[CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 218735182-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamideHCID 22728543Water ethylacetate

생성물 1

HCID 218735118-Bromo-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one수율 84.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
150 °C

실험 절차

The 2-bromo-N-(3-bromo-2-hydroxy-phenyl)-2-methyl-propionamide of step 1 was dissolved in DMF (200 ml), and to the DMF solution was added to K2CO3 (6.3 g, 45.58 mmol). The mixture was heated overnight at 150° C., then cooled and poured into a mixture of water/ethyl acetate. The organic fraction was washed with brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 8-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one as a white solid (84.6%). MS: (M−H)− 256.

후처리

  1. temperaturecooled
  2. washThe organic fraction was washed with brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo
  5. customresulting brown residue
  6. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-89a2c7c3c4004b8e8d01f4948e3b7480
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202241B2

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