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

HRID 1730723Notes

Reaction equation

HRID 1730723 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].C1(C)C=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 1140TolueneHCID 14798Sodium HydroxideHCID 24408BromineHCID 69276Benzene, 1-(dibromomethyl)-4-nitro-

Product 1

HCID 149217151-Nitro-4-(tribromomethyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 100 parts of p-nitrobenzal bromide in 500 parts of toluene is added to a solution of 80 parts of bromine plus 160 parts of 50% sodium hydroxide in a 1,000 parts of water at 50° C. The mixture is stirred mechanically at 50° C for 10 hours. The toluene layer is separated; the water layer is extracted with 500 parts of toluene. The combined toluene layers are dried and evaporated to give 110 parts (85% yield) of p-nitrobenzotribromide, m.p. 74°-81° C.

Workup

  1. customThe toluene layer is separated
  2. extractionthe water layer is extracted with 500 parts of toluene
  3. dry with materialThe combined toluene layers are dried
  4. customevaporated

Sources & evidence

ORD record
ord-f9312140dce04ec291923ab351266963
Source dataset
uspto-grants-1976_11
Patent number
US03993704

Reaction notes

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