Potassium Hydroxide → HCID 21966445, compound

HRID 2212601Notes

Reaction equation

HRID 2212601 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-c8193918f13e477ab29e7477de911aa5
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

Loading…