Phosphorus tribromide → 2,3-Dichloro-5-nitrophenylmethyl bromide

HRID 274845Notes

Reaction equation

HRID 274845 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12]O.P(Br)(Br)[Br:15]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][Br:15]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 214781232,3-Dichloro-5-nitrobenzyl alcohol

Product 1

HCID 214781122,3-Dichloro-5-nitrophenylmethyl bromideYield 230.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the method of Example 1, Step B, 61.90 grams (0.279 mole) of 2,3-dichloro-5-nitrophenylmethanol and 26.41 grams (0.098 mole) of phosphorus tribromide were reacted in 800 mL of toluene, yielding 64.38 grams of 2,3-dichloro-5-nitrophenylmethyl bromide as a golden oil which solidified upon standing. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-134abae0d5b74e77ba0af22bc0934590
Source dataset
uspto-grants-1995_02
Patent number
US05391541

Reaction notes

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