Potassium Hydroxide → HCID 21966445, compound

HRID 1790204Notes

Reaction equation

HRID 1790204 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH2:4].[OH-].[K+].[C:14](Cl)(=[O:18])[CH:15]([CH3:17])[CH3:16]>ClCCl>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH:4][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 62325Isobutyryl chlorideHCID 21966452HCID 21966452, compound

Product 1

HCID 21966445HCID 21966445, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a biphasic mixture of 2-bromo-5-methoxy-4-methyl-aniline (5.6 g, 25.96 mmol), 10% KOH (27 mL) and dichloromethane (30 mL), was added dropwise isobutyryl chloride (3 mL, 28.55 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 48 hrs. The layers were separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated to give 7.38 g of N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (99% yield). 1H NMR (300 MHz; CDCl3): 1.29 (d, J=6.9 Hz, 6 H), 2.14 (s, 3 H), 2.59 (m, 1 H), 3.84 (s, 3 H), 7.24 (s, 1 H), 7.66 (br s, 1 H), 8.07 (s, 1 H).

Workup

  1. customThe layers were separated
  2. extractionThe aqueous layer was further extracted with dichloromethane
  3. washthe combined organics washed successively with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bce456ac6a614e5089098c99135f35ff
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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