Synthesis of 3-(4-bromophenyl)-1-propene

Preparation of 3-(4-bromophenyl)-1-propene

A solution of 130 g. (1.08 moles) of allyl bromide in twice its volume of dry ether is added dropwise to an ethereal solution of p-bromo-phenylmagnesium bromide prepared from 1.0 mole (237 g.) of p-dibromobenzene and 27 g. (1.1 gram atoms) of magnesium. The mixture is then heated to reflux for 30 minutes, followed by the drop-wise addition of excess water to the cooled mixture. The ether is distilled off, and the residue is steam-distilled to remove the p-bromo-allylbenzene. The product is separated from the distillate, dried over calcium chloride, and distilled twice through a Vigreux column to give 128-130 g. of p-bromoallylbenzene, b.p. 95-96°/12 mm. The yield is 66% based on bromobenzene.

Reference: Bull, soc chim. France, (4), 45, 78 (1929).

IUPAC Name

1-bromo-4-prop-2-enylbenzene

InChI

InChI=1S/C9H9Br/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7H,1,3H2

InChI Key

LIGHOIDTGDLAKK-UHFFFAOYSA-N

Canonical SMILES

C=CCC1=CC=C(C=C1)Br

Depositor-Supplied Synonyms

3-(4-Bromophenyl)-1-propene, 2294-43-1, Benzene, 1-bromo-4-(2-propenyl)-, 1-Allyl-4-bromobenzene, 4-(Prop-1-en-3-yl)bromobenzene, OR01868, 4-allylbromobenzene, 4-allyl-bromobenzene, 4-Allylphenyl bromide, AC1L3ASI, 1-Ally1-4-bromobenzene, 1-allyl-4-bromo-benzene, SCHEMBL648420, 1-bromo-4-prop-2-enylbenzene, 3-(4-Bromophenyl)prop-1-ene, SCHEMBL10110637, CTK4F0519, DTXSID80177481, LIGHOIDTGDLAKK-UHFFFAOYSA-N, MolPort-001-756-654, ZINC2245280, ZX-AT019459, 7818AD, MFCD01319542, 1-bromo-4-(prop-2-en-1-yl)benzene, AKOS016016679, ACM2294431, FCH1121771, Benzene,1-bromo-4-(2-propen-1-yl)-, AK177695, OR091457, KB-177945, 10005-031a

Removed Synonyms

C9H9Br, CID137529

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