Water → Benzene, 1,1'-(bromomethylene)bis(4chloro-

HRID 602649

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.B(Br)(Br)[Br:18].O>C(Cl)Cl>[Br:18][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 15.14 g (59.3 mmol) of bis(4-chlorophenyl)methanol in 100 mL of methylene chloride was added slowly a solution of 71.2 mL of BBr3 (71.2 mmol, 1M in CH2Cl2). The solution was stirred for at 0° C. for 1 h. Then 60 mL of water was added to quench the reaction and the reaction mixture was poured into 200 mL of methylene chloride. The water layer was extracted with methylene chloride (60 mL×2) and the combined organic layer was dried over Na2SO4 and concentrated to give the title compound; 1NMR (CDCl3) δ 6.24 (s, 1H), 7.36 (d, 4H, J=8.7 Hz), 7.41 (d, 2H, J=8.7 Hz).

Workup

customto quench
customthe reaction
extractionThe water layer was extracted with methylene chloride (60 mL×2)
dry with materialthe combined organic layer was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-c1e0e25b637a443faee5108660cb8b11
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906503B2

Linked notes

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