Triphenylphosphine → 1-Bromo-3,5-di-tert-butylbenzene

HRID 1071197Notes

Reaction equation

HRID 1071197 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[C:22]([C:26]1[CH:27]=[C:28](O)[CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:31]=1)([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[Br:20][C:28]1[CH:27]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408Bromine2×HCID 708253,5-Di-tert-butylphenol

Product 1

HCID 6201361-Bromo-3,5-di-tert-butylbenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A 1000 ml three-neck, round-bottom flask was equipped with a mechanical stirrer, a pressure-compensating dropping funnel, and a reflux condenser. A nitrogen gas flow adapter with overpressure valve was attached on top of the reflux condenser. A slight nitrogen flow guaranteed an inert gas atmosphere in the apparatus. The flask was charged with 181 g triphenylphosphine (690 mmol) and 160 mL acetonitrile (HPLC grade). The white suspension was cooled in an ice bath for 15 minutes. While stirring, dropwise addition of 101.5 g bromine (635 mmol) took place within 40 minutes. After bromine addition, the ice bath was removed. 124 g of 3,5-di-tertbutylphenol (601 mmol) and 140 mL acetonitrile were added in one portion. The orange/white suspension converted into an orange solution upon heating. The mechanical stirrer was replaced by an egg-shape stir bar. The solution was stirred at gentle reflux temperature for three hours.

Workup

  1. customA 1000 ml three-neck, round-bottom flask was equipped with a mechanical stirrer
  2. customA nitrogen gas flow adapter with overpressure valve was attached on top of the reflux condenser
  3. temperatureThe white suspension was cooled in an ice bath for 15 minutes
  4. customwithin 40 minutes
  5. customthe ice bath was removed
  6. temperatureupon heating
  7. stirringstir bar
  8. stirringThe solution was stirred at gentle reflux temperature for three hours

Sources & evidence

ORD record
ord-c6afd8ea2fae43a7bb66ca68be85b45d
Source dataset
uspto-grants-2005_06
Patent number
US06903229B2

Reaction notes

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