Dimethylformamide → 2-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrile

HRID 859667

반응식

HRID 859667 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([F:13])[CH:5]=1.I[CH3:15].C[N:17]([CH:19]=O)C>C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:15])([CH3:11])[C:19]#[N:17])=[C:6]([F:13])[CH:5]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

생성물 1

HCID 534036182-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrile

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.82 g, 20.6 mmol) in DMF (20 mL) cooled to 0° C. was added a solution of (4-bromo-2-fluoro-phenyl)-acetonitrile (2.0 g, 9.35 mmol) from Step 1 above, dissolved in THF (10 mL). The reaction was stirred till gas evolution ceased, and then iodomethane (1.3 mL, 20.6 mmol) was added slowly. The reaction was stirred for 30 minutes, and then diluted with 100 mL EtOAc. The solids were removed by filtration, and the organic layer was washed with 100 mL water. The organic layer was dried over MgSO4, and then filtered. The mother liquor was concentrated by rotary evaporation, and the product was distilled under high vacuum (0.3 torr, 45° C.). Yield: 2.25 g, 99%. %. 1H NMR (CDCl3) δ: 2.81 (s, 3H), 2.88 (s, 3H), 7.20–7.25 (m, 3H).

후처리

  1. stirringThe reaction was stirred for 30 minutes
  2. customThe solids were removed by filtration
  3. washthe organic layer was washed with 100 mL water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe mother liquor was concentrated by rotary evaporation
  7. distillationthe product was distilled under high vacuum (0.3 torr, 45° C.)

출처 및 근거

ORD 기록
ord-b5d483ffac8341c4bc7b9a479c597a61
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151105B2

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