Pyridine → N-(2-Bromo-6-fluorophenyl)pivalamide

HRID 1172359ノート

反応式

HRID 1172359 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].N1C=CC=CC=1.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

参加物

4

反応物 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 27829402-Bromo-6-fluoroaniline

生成物 1

HCID 44203089N-(2-Bromo-6-fluorophenyl)pivalamide収率 76%

実験手順

2-Bromo-6-fluoroaniline (43.2 mmol, 8.2 g) was dissolved in pyridine (124 mmol, 10 mL). Pivaloyl chloride (57.15 mmol, 7.0 mL) was added to the mixture. Reaction was stirred at room temperature for 3 hours. Reaction mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed 2×1N HCl, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was treated with hexanes and triturated. Resulting solids were filtered off, washed with hexanes then dried in vacuo. Title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): δ=7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). MS m/e (M+H)+=274.1, 276.1.

後処理

  1. customReaction
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionResidue was treated with ethyl acetate (50 mL)
  5. washMixture was washed 2×1N HCl, 1× brine
  6. dry with materialOrganic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionResidue was treated with hexanes
  10. customtriturated
  11. customResulting solids
  12. filtrationwere filtered off
  13. washwashed with hexanes
  14. customthen dried in vacuo

出典と根拠

ORDレコード
ord-bcb7399423cf4f0394870dcfe7ea67ef
出典データセット
uspto-grants-2010_11
特許番号
US07834007B2

反応ノート

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