1,2,3-Trimethoxybenzene → 1-Bromo-2,3,4-trimethoxybenzene

HRID 1836800Notes

Reaction equation

HRID 1836800 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:7]([O:8][CH3:9])[C:4]=1[O:5][CH3:6].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][C:12]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 124621,2,3-TrimethoxybenzeneHCID 67184N-bromobutanimide

Product 1

HCID 2569301-Bromo-2,3,4-trimethoxybenzeneYield 78.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Pyrogallol trimethyl ether (5.1 g) was suspended in CCl4 (60 mL) and N-bromosuccinimide (6.5 g, 1.2 eq.) was added. The reaction mixture was heated at reflux for 20 hours. The succinimide was collected and the filtrate concentrated in vacuo to a brown oil. The oil was separated by gravity column chromatography (hexane-ethyl acetate, 19: 1) and yielded the title compound as a yellow oil (5.9 g, 78%): EIMS m/z 234 ((M+ —CH3, 81Br), 232 (M+ —CH3, 79Br), 107, 95, 69, 58, 44; 1H NMR (CDCl3, 300 MHZ) δ 7.21 (1H, d, J=9.0 Hz, H6), 6.58 (1H, d, J=9.0 Hz, H5), 3.91 (3H, s, OCH3), 3.89 (3H, s, OCH3), 3.85 (3H, s, OCH3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. customThe succinimide was collected
  4. concentrationthe filtrate concentrated in vacuo to a brown oil
  5. customThe oil was separated by gravity column chromatography (hexane-ethyl acetate, 19: 1)

Sources & evidence

ORD record
ord-373e70f9e8e9479c96907cd4bce8d758
Source dataset
uspto-grants-2004_08
Patent number
US06777578B2

Reaction notes

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