Benzene → 2-(Bromomethyl)-4-chloro-1-iodobenzene

HRID 1388545Notes

Reaction equation

HRID 1388545 reaction equation
P(Br)(Br)[Br:2].C1C=CC=CC=1.N1C=CC=CC=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([I:26])=[C:22]([CH:25]=1)[CH2:23]O>C(Cl)(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([I:26])=[C:22]([CH:25]=1)[CH2:23][Br:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 24614Phosphorus tribromideHCID 818020(5-Chloro-2-iodophenyl)methanol

Product 1

HCID 98623842-(Bromomethyl)-4-chloro-1-iodobenzeneYield 247.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 41.6 g of phosphorus tribromide, 25 ml of benzene and 8.2 ml of pyridine is prepared while cooling and while stirring it is treated dropwise at a maximum temperature of 10° C. with 108.3 g of 5-chloro-2-iodobenzyl alcohol. Then, it is stirred for 4 hours at room temperature and for 1 hour at 50° C. After cooling, it is diluted with 120 ml of chloroform, the mixture washed with 25 ml of 5% hydrochloric acid, a 5% sodium hydroxide solution and with water, dried with magnesium sulfate and evaporated. There are obtained 126 g (95%) of crude 5-chloro-2-iodobenzyl bromide melting at 75°-79° C. The pure product is obtained by crystallization from a mixture of benzene and petroleum ether, m.p. 77°-79° C.

Workup

  1. customis prepared
  2. temperaturewhile cooling
  3. stirringThen, it is stirred for 4 hours at room temperature and for 1 hour at 50° C
  4. temperatureAfter cooling
  5. washthe mixture washed with 25 ml of 5% hydrochloric acid
  6. dry with materiala 5% sodium hydroxide solution and with water, dried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-56f5d6592a42441684f0adcd10d8f599
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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