3-Bromo-5-(trifluoromethyl)benzoic acid → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 623829ノート

反応式

HRID 623829 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:15]([Cu])#[N:16].CO.ClCCl>CN(C=O)C>[C:15]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:16]

参加物

5

反応物 3

HCID 110867883-Bromo-5-(trifluoromethyl)benzoic acidHCID 21226129Dichloromethane methanolHCID 178418546HCID 178418546、化合物

生成物 1

HCID 589022873-Cyano-5-(trifluoromethyl)benzoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

In a 3-neck 100 mL round-bottomed flask, 3-bromo-5-(trifluoromethyl)benzoic acid (10.0, 1.0 eq.) was dissolved in DMF (100 mL, 10 Vol). CuCN was added at RT and the reaction was stirred at 150° C. for 15-16 hr. Reaction completion was monitored on TLC using MeOH:dichloromethane (1:9) mobile phase. Reaction mixture was quenched into the ice-water slurry (1000 mL) and filtered over celite. Compound was extracted in the ethyl acetate (250 mL×3). Organic layer was washed with water (150 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure. Then again the crude was dissolved in ethyl acetate and extracted with (250 mL×3). Combined aqueous layer was again acidified with dil HCl (350 mL) to get pH 3. Then aqueous layer was extracted with ethyl acetate (250 mL×3). This combined organic layer was washed with water (150 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 6.0 g of crude compound, Yield (75.4%). This crude material was directly used for next step without purification; Mass: (ES−) 214.14 (M−1).

後処理

  1. customReaction completion
  2. customReaction mixture
  3. customwas quenched into the ice-water slurry (1000 mL)
  4. filtrationfiltered over celite
  5. extractionCompound was extracted in the ethyl acetate (250 mL×3)
  6. washOrganic layer was washed with water (150 mL)
  7. customby drying
  8. concentrationOrganic layer was concentrated under reduced pressure
  9. dissolutionThen again the crude was dissolved in ethyl acetate
  10. extractionextracted with (250 mL×3)
  11. customto get pH 3
  12. extractionThen aqueous layer was extracted with ethyl acetate (250 mL×3)
  13. washThis combined organic layer was washed with water (150 mL)
  14. customby drying
  15. concentrationOrganic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-e8fbdca36ff44553bfd7f95cc2cab1a9
出典データセット
uspto-grants-2016_04
特許番号
US09303000B2

反応ノート

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