Methyl iodide → 6-(3-bromo-4-fluoro-benzoyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 469334노트

반응식

HRID 469334 반응식
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[F:23])[C:7]([C:9]1[CH:18]=[C:17]([CH3:19])[C:12]2[NH:13][C:14](=[O:16])[O:15][C:11]=2[CH:10]=1)=[O:8].I[CH3:25]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[F:23])[C:7]([C:9]1[CH:18]=[C:17]([CH3:19])[C:12]2[N:13]([CH3:25])[C:14](=[O:16])[O:15][C:11]=2[CH:10]=1)=[O:8]

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 24758Sodium hydrideHCID 581811656-(3-bromo-4-fluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one

생성물 1

HCID 581811086-(3-bromo-4-fluoro-benzoyl)-3,4-dimethyl-3H-benzoxazol-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.175 g (4.00 mmol) sodium hydride (55%, suspension in mineral oil) were added at RT to 1.33 g (3.80 mmol) 6-(3-bromo-4-fluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one in 5 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.317 mL (5.00 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then 0.100 mL (15.8 mmol) iodomethane were added and the mixture was stirred overnight at RT. After the addition of ice water the reaction mixture was extracted with EtOAc. The organic phase was washed with water, dried on sodium sulphate and evaporated down i. vac. The residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down and dried i. vac.

후처리

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringthe mixture was stirred overnight at RT
  3. extractionwas extracted with EtOAc
  4. washThe organic phase was washed with water
  5. customdried on sodium sulphate
  6. customevaporated down i
  7. customThe residue was purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down
  10. customdried i

출처 및 근거

ORD 기록
ord-779b417fe0214c84a4eb15c9959a5219
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629137B2

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