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

HRID 1724164Notes

Reaction equation

HRID 1724164 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

5

Reactant 3

HCID 962WaterHCID 70334,4'-DichlorobenzhydrolHCID 25134Boron tribromide

Product 1

HCID 95197Benzene, 1,1'-(bromomethylene)bis(4chloro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

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

Sources & evidence

ORD record
ord-69daa1b6af3b4e4e9260bc2d3a1b6185
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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