Pivaloyl chloride → N-(2-Bromo-6-fluorophenyl)pivalamide

HRID 501980Notes

Reaction equation

HRID 501980 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[C:10](Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 27829402-Bromo-6-fluoroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Bromo-6-fluoroaniline (8.2 g, 43.2 mmol) was dissolved in pyridine (10 mL) and treated with pivaloyl chloride (7.0 mL, 57.2 mmol). The reaction was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo and treated with ethyl acetate (50 mL). Mixture was washed 1 N hydrochloric acid (2×), then brine. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with hexanes to give a solid which was filtered, washed with hexanes, and dried in vacuo. The 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). Mass spec.: 274.1 (MH)+, 276.1 (MNa)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiontreated with ethyl acetate (50 mL)
  3. washMixture was washed 1 N hydrochloric acid (2×)
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexanes
  8. customto give a solid which
  9. filtrationwas filtered
  10. washwashed with hexanes
  11. customdried in vacuo

Sources & evidence

ORD record
ord-7ddfd415933c4918aca2389001d26553
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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