4,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl → 3,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepine

HRID 1185632Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[CH2:15]O)=[C:4]([CH2:17][OH:18])[CH:3]=1>P(=O)(O)(O)O.O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH2:17][O:18][CH2:15][C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 160 °C

Procedure

The suspension of (4,4′-dibromo-2′-hydroxymethyl-biphenyl-2-yl)-methanol (460 mg) in phosphoric acid (25 ml) was heated at 160° C. for 4 hours. The mixture was cooled and diluted with water (100 ml), and was extracted with EtOAC. The organic phase was washed with water, saturated sodium bicarbonate, and brine, and was dried with sodium sulfate. Concentration yielded 3,9-dibromo-5,7-dihydro-dibenzo[c,e]oxepine (416 mg).

Workup

temperatureThe mixture was cooled
extractionwas extracted with EtOAC
washThe organic phase was washed with water, saturated sodium bicarbonate, and brine
dry with materialwas dried with sodium sulfate
concentrationConcentration

Sources & evidence

ORD record: ord-7fa42e3bb7ce4ed09284b8fba344ec82
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669234B2

Reaction notes

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