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

HRID 249160

Reaction equation

HRID 249160 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.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[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)[Br:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70334,4'-DichlorobenzhydrolHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 95197Benzene, 1,1'-(bromomethylene)bis(4chloro-Yield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bis(4-chlorophenyl)methanol (2.0 g) and carbon tetrabromide (5.2 g) in tetrahydrofuran (30 ml) was added triphenylphosphine (4.2 g). The mixture was stirred at room temperature for 1 hours. After the mixture was filtered off, the solvent was removed in vacuo. The residue was dissolved in n-hexane (30 ml) and filtered off. The filtrate was evaporated and the residue was purified by distillation at reduced pressure to give bis(4-chlorophenyl)bromomethane as an oil (2.43 g).

Workup

  1. filtrationAfter the mixture was filtered off
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in n-hexane (30 ml)
  4. filtrationfiltered off
  5. customThe filtrate was evaporated
  6. distillationthe residue was purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-07c610984f97440caba6c4521e6c61f0
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Linked notes

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