Triphenylphosphine → 1-(Bromomethyl)-3,5-dichlorobenzene

HRID 2232701Notes

Reaction equation

HRID 2232701 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:24]O.[Br:30]C(Cl)(Cl)C(Cl)(Cl)Br>C(OCC)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:24][Br:30]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 432363,5-Dichlorobenzylic alcoholHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethane

Product 1

HCID 125839781-(Bromomethyl)-3,5-dichlorobenzeneYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of triphenylphosphine (8.1 g) in diethyl ether (100 cm3) was added to a stirred solution of 3,5-dichlorobenzyl alcohol (5 g) and 1,2-dibromotetrachloroethane (9.9 g) in diethyl ether whilst maintaining the reaction temperature below 5° C. When the addition was complete the reaction mixture was allowed to warm to the ambient temperature (ca. 25° C.), and the mixture stirred for a further 2 hours. The precipitated solid was removed by filtration, and the filtrate concentrated by evaporation of the solvent to give 3,5-dichlorobenzyl bromide (6.8 g).

Workup

  1. temperaturewhilst maintaining the reaction temperature below 5° C
  2. additionWhen the addition
  3. customThe precipitated solid was removed by filtration
  4. concentrationthe filtrate concentrated by evaporation of the solvent

Sources & evidence

ORD record
ord-e35ac25b89324717bfe86fc6a49eef07
Source dataset
uspto-grants-1988_11
Patent number
US04788348

Reaction notes

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