1,2-Dibromoethane → 1-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

HRID 858601ノート

反応式

HRID 858601 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[C:6]([F:13])[CH:5]=1.Br[CH2:15][CH2:16]Br>CN(C=O)C.C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:16][CH2:15]2)=[C:6]([F:13])[CH:5]=1

参加物

7

反応物 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

生成物 1

HCID 587623291-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 1,2-dibromoethane (1.8 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: 0.98 g, 44%.

後処理

  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.)

出典と根拠

ORDレコード
ord-12711fcd3fee41e5987003e9d6875ff4
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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