2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 7-bromobenzo[b]oxepin-5(2H)-one

HRID 1408793Notes

Reaction equation

HRID 1408793 reaction equation
N1C(C)=CC(C)=CC=1C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[Br:24][C:25]1[CH:43]=[CH:42][C:28]2[O:29][CH2:30][CH2:31][CH:32]=[C:33]([O:34][Si](C(C)(C)C)(C)C)[C:27]=2[CH:26]=1>C1(C)C=CC=CC=1>[Br:24][C:25]1[CH:43]=[CH:42][C:28]2[O:29][CH2:30][CH:31]=[CH:32][C:33](=[O:34])[C:27]=2[CH:26]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 79532,4,6-TrimethylpyridineHCID 67174387HCID 67174387, compound

Product 1

HCID 542267847-bromobenzo[b]oxepin-5(2H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4,6-Collidine (5.6 ml), DDQ (9.0 g, 40 mmol) and (7-bromo-2,3-dihydrobenzo[b]oxepin-5-yloxy)(tert-butyl)dimethylsilane was dissolved in toluene, the mixture was stirred for 5.5 hours at room temperature. the mixture was concentrated in vacuo and then purified by column chromatography to give 7-bromobenzo[b]oxepin-5(2H)-one (4.5 g, 94%). 1H-NMR (MeOD): 4.71 (m, 2H), 6.38 (m, 1H), 6.76 (m, 1H), 6.99 (m, 1H), 7.54 (m, 1H), 8.06 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-7cbacb6115b2421fb34f601dc4cd8c28
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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