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

HRID 469334ノート

反応式

HRID 469334 の反応式
[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]

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 24758Sodium hydrideHCID 581811656-(3-bromo-4-fluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-779b417fe0214c84a4eb15c9959a5219
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

反応ノート

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