ChemicalBook CAS DataBase List 4,4'-Bis(bromomethyl)biphenyl

4,4'-Bis(bromomethyl)biphenyl synthesis

11synthesis methods

Product Name:4,4'-Bis(bromomethyl)biphenyl
CAS Number:20248-86-6
Molecular formula:C14H12Br2
Molecular Weight:340.05

1667-12-5 Synthesis

1667-12-5
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1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE

65946-59-0
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Yield:65946-59-0 92.2%

Reaction Conditions:

with sulfuric acid;hydrogen bromide in water;

Steps:

b b)

b) Preparation of 4,4'-Bis (Bromomethyl) Biphenyl. 11.6g (54.13 mmoles) of 4,4'-bis (hydroxymethyl) biphenyl, 35.3 ml of HBr at 48% by weight in H₂O (649.6 mmoles) and 19.11 ml of H₂SO₄ at 96% are placed in a three-necked 500ml flask which has a mechanical agitator, cooler and oil heating bath. The mixture is heated to 135^oC under vigorous agitation for 4 hours, after the first two hours adding to the very dense mixture an additional 7.4ml of HBr at 48% and 2ml of H₂SO₄ at 96%. On completion the cooled mixture is filtered on a Gooch G2 and the precipitate recovered is washed with iced water until the washings are neutral (about 1 litre). The solid residue is extracted with three 100ml-portions of hot toluene (50^oC) and the extract is filtered hot. The toluene solution is concentrated dry at a reduced pressure and the residue dried at 40^oC using a high-vacuum pump. 16.97g of 4,4'-bis (bromomethyl) biphenyl are obtained with a molar yield of 92.2%.

References:

EP469682,1992,A1

613-33-2 Synthesis