Antimony pentachloride → 1-Bromo-3-(heptafluoropropyl)benzene

HRID 437452

Reaction equation

[Sb](Cl)(Cl)(Cl)(Cl)Cl.[F:7][C:8]([F:22])([C:18]([F:21])([F:20])[F:19])[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([F:11])[F:10].[Br:23]Br.ClCl.S(=O)(O)[O-].[Na+]>O>[Br:23][C:14]1[CH:13]=[C:12]([C:9]([F:11])([F:10])[C:8]([F:22])([F:7])[C:18]([F:19])([F:20])[F:21])[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 26 °C

Procedure

First meta-bromo(heptafluoropropyl)benzene is prepared as follows. 12 g (0.04 mole) of antimony pentachloride are added to 389 g (1.58 mole) of heptafluoropropylbenzene and then, with intensive stirring, 41 ml (0.79 mole) of bromine are added in drops within an hour with simultaneously cooling the reaction mixture on a water bath. The temperature of the reaction mixture is maintained at 26° C maximum. After adding all the bromine, the reaction mixture is given another stirring for 15 minutes. In the course of the entire bromination reaction, dry chlorine is passed into the reaction mixture at a rate of 3 liters per hour. On completion of the reaction, for binding the unreacted bromine, the reaction mixture is poured into 500 ml of water containing 25 ml of saturated solution of sodium bisulphite. The reaction product is distilled with steam, neutralized with a 5 percent solution of sodium hydroxide dried over calcined calcium chloride, and rectified. The yield of meta-bromo(heptafluoropropyl)benzene is 447.2 g (87 percent of theory).

Workup

temperaturewith simultaneously cooling the reaction mixture on a water bath
customstirring for 15 minutes
customOn completion of the reaction
distillationThe reaction product is distilled with steam
customdried

Sources & evidence

ORD record: ord-3e31385bf48f4be7a2ae10e4976f962d
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04031119

Linked notes

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