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

HRID 437452
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 24294Antimony pentachlorideHCID 24408Bromine3×HCID 24526ChlorineHCID 13418746(Heptafluoropropyl)benzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 214284281-Bromo-3-(heptafluoropropyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

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

Sources & evidence

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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes