N-bromobutanimide → 1-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene

HRID 2268438Notes

Reaction equation

HRID 2268438 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[C:3]=1[O:15][CH3:16].[Br:17]N1C(=O)CCC1=O>CC(N=NC(C#N)(C)C)(C#N)C.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH2:8][Br:17])=[C:6]([O:9][CH3:10])[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[C:3]=1[O:15][CH3:16]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 125607691-Bromo-2,3,4,5-tetramethoxy-6-methylbenzene

Product 1

HCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzeneYield 99.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8857Ethyl AcetateSolvent

Procedure

An ethyl acetate (300 ml) solution of 1-bromo-2,3,4,5-tetramethoxy-6-methylbenzene (49.5 g, 0.170 mols), N-bromosuccinimide (31.8 g, 0.179 mols) and AIBN (558 mg, 3.40 mmols) was heated under reflux for 1 hour. The reaction mixture was concentrated in vacuo, and then diluted with hexane. The resulting crystals were separated by filtration, and the filtrate was concentrated to obtain the entitled compound (62.6 g) as an oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with hexane
  4. customThe resulting crystals were separated by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5e97f78620604b55a49a76458f60ea52
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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