Triethylamine → 4-Bromo-2,6-dimethoxy-phenyl-3,3-dimethyl-butanamide

HRID 880702Notes

Reaction equation

HRID 880702 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](N)=[C:6]([O:8][CH3:9])[CH:7]=1.C([N:15](CC)CC)C.[C:20]([CH2:24][C:25](Cl)=[O:26])([CH3:23])([CH3:22])[CH3:21]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([CH:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:25]([NH2:15])=[O:26])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 3294234-Bromo-2,6-dimethoxyaniline

Product 1

HCID 866496364-Bromo-2,6-dimethoxy-phenyl-3,3-dimethyl-butanamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the crude 5-bromo-1,3-dimethoxy-2-amino-benzene from above and triethylamine (1.5 g, 15 mmol) in anhydrous dichloromethane (50 mL) was added dropwise tert-butyl acetyl chloride (1.6 g, 12 mmol) with stirring at room temperature. The reaction mixture was stirred for 3 hours at room temperature. Then the reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min) to give a white solid (3.0 g, 91%). 1H-NMR (DMSO-d6, 400 MHz): δ 8.69 (brs, 1H, exchangeable with D20), 6.87 (s, 2H), 3.73 (s, 6H), 2.11 (s, 2H), 1.02 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred for 3 hours at room temperature
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min)

Sources & evidence

ORD record
ord-59cb6c3e93094a428531bc36b591f3f5
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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