Methanol → beta-Bromostyrene

HRID 1658980Notes

Reaction equation

HRID 1658980 reaction equation
C(OOC(C)(C)C)(C)(C)C.CO.[Br:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1Br>>[Br:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8033Di-tert-butyl peroxideHCID 3340691-Bromo-2-(2-bromoethyl)benzene

Product 1

HCID 7667beta-Bromostyrene

Procedure

A quantity of 2 g of di-tertbutyl peroxide was dissolved in 100g of β-bromoethyl bromobenzene and the solution was added through a motor-driven syringe into the reactor at a rate of 60g/h, together with 25 g of methanol and with nitrogen which was passed in at a rate of 2 l/h. The reactor used in this example was a glass spiral made of 6 mm wide and 5 m long tube heated to 300°-320°C. The products were collected in a trap immersed in an ice bath while the methyl bromide was trapped in a container positioned in liquid nitrogen. The liquid products were then subjected to fractional distillation under vacuum. There were obtained 58 g bromostyrene and 12 g unconverted reactant. The yield was 95% bromostyrene.

Workup

  1. temperature5 m long tube heated to 300°-320°C
  2. customThe products were collected in a trap
  3. customimmersed in an ice bath while the methyl bromide
  4. distillationThe liquid products were then subjected to fractional distillation under vacuum

Sources & evidence

ORD record
ord-d80421d550ae43ffa4be1ae8402cd9fd
Source dataset
uspto-grants-1976_06
Patent number
US03966831

Reaction notes

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