Chlorobenzene → 1-Nitro-4-(tribromomethyl)benzene

HRID 1730724Notes

Reaction equation

HRID 1730724 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]([Br:10])[Br:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC1C=CC=CC=1.[Br:20]Br.[OH-].[Na+]>O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([Br:20])([Br:9])[Br:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 14798Sodium HydroxideHCID 24408BromineHCID 69276Benzene, 1-(dibromomethyl)-4-nitro-

Product 1

HCID 149217151-Nitro-4-(tribromomethyl)benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 100 parts of p-nitrobenzal bromide in 1,000 parts of chlorobenzene is stirred with a solution of 80 parts of bromine plus 160 parts of 50% sodium hydroxide in 1,000 parts of water at 50° C for 10 hours. The bottom layer is separated and evaporated to dryness to give 110 parts (86% yield) of p-nitrobenzotribromide, m.p. 66°-70° C.

Workup

  1. customThe bottom layer is separated
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-4b35b7e3988043b1b6773593e70c5614
Source dataset
uspto-grants-1976_11
Patent number
US03993704

Reaction notes

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