Carbon Tetrachloride → 2-bromo-1-chloro-4-(chloromethyl)benzene

HRID 2265309Notes

Reaction equation

HRID 2265309 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:31]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][Cl:31]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 50998689(3-Bromo-4-chlorophenyl)methanol

Product 1

HCID 687704272-bromo-1-chloro-4-(chloromethyl)benzeneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-chlorobenzyl alcohol (9.6 g, 43 mmol) in CH2Cl2 (100 mL) was added Ph3P (17.1 g, 1.5 mmol) and CCl4 (6.3 mL, 65 mmol). After 18 h, the solution was washed with brine (3×100 mL) and passed through a short silica gel column to afford the product as colorless oil (9.14 g, 88%). 1H NMR (400 MHz, CDCl3): 7.65 (d, J=2.1 Hz, 1H), 7.43 (d, J=8.2 Hz, 1H), 7.27 (dd, J=8.3, 2.1 Hz, 1H), 4.51 (s, 3H).

Workup

  1. washthe solution was washed with brine (3×100 mL)

Sources & evidence

ORD record
ord-690983d849f54193a80e1f7e8bbc4f15
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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