N-bromobutanimide → 3-Bromo-2,6-dimethoxytoluene

HRID 1816412Notes

Reaction equation

HRID 1816412 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(#N)C>[Br:12][C:8]1[CH:7]=[CH:6][C:5]([O:9][CH3:10])=[C:4]([CH3:11])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 797552,6-Dimethoxytoluene

Product 1

HCID 108897433-Bromo-2,6-dimethoxytolueneYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,3-dimethoxy-2-methylbenzene (1.86 g, 12.2 mmol) and N-bromo-succinimide (2.17 g, 12.2 mmol) in acetonitrile (30 mL) was stirred at 60° C. for 20 h. After most of the solvent was removed in vacuo, extraction in ethyl ether (2×75 mL) with water (2×50 mL) and flash chromatography with silica gel (gradient to 5% ether/hexanes) provided the title compound as a colorless liquid (2.51 g, 89% yield): 1H NMR (300 MHz, CDCl3) δ 2.19 (s, 3H), 3.78 (s, 3H), 3.81 (s, 3H), 6.54 (d, 1H, J=8.8 Hz), 7.32 (d, 1H, J=8.8 Hz).

Workup

  1. customAfter most of the solvent was removed in vacuo, extraction in ethyl ether (2×75 mL) with water (2×50 mL) and flash chromatography with silica gel (gradient to 5% ether/hexanes)

Sources & evidence

ORD record
ord-6018ec0071c1406fb5066dad7fd3d2c5
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

Loading…