HCID 21966470, compound → HCID 21966445, compound

HRID 2212610Notes

Reaction equation

HRID 2212610 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[CH3:9].[Br-:16].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:16][C:6]1[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH:10][C:11](=[O:15])[CH:12]([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 21966470HCID 21966470, compoundHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 21966445HCID 21966445, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-methoxy-4-methyl-phenyl)-isobutyramide (5.0 g, 24.1 mmol) in dichloromethane (200 mL) was added tetrabutylammonium tribromide (12.2 g, 25.3 mmol) at 0° C. The mixture was then stirred at room temperature for 20 hours. The solution was washed with water, brine, aqueous sodium bicarbonate solution, brine, dried over MgSO4, filtered and evaporated under reduced pressure to give 6.83 g of N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (99%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.29 (d, J=7.03 Hz, 6 H), 2.15 (s, 3 H), 2.59 (m, 1 H), 3.84 (s, 1 H), 7.24 (s, 1 H), 7.65 (bs, 1 H), 8.08 (s, 1 H).

Workup

  1. washThe solution was washed with water, brine, aqueous sodium bicarbonate solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7daf52d7f33844489f803b64c441dd38
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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