Bromobenzene → 2-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acid

HRID 1386846Notes

Reaction equation

HRID 1386846 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].BrC1C=CC=CC=1.[C:12]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][C:13]1=[CH2:14].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1>>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:16](=[O:17])[CH2:15][C:13](=[CH2:14])[C:12]([OH:18])=[O:19])=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 163234-ChlorobiphenylHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 98393182-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acidYield 50%

Conditions

Temperature
0 °C

Procedure

21.2 g of anhydrous aluminum chloride are introduced into 50 g of bromobenzene and the mixture is cooled to 0° C. A solid mixture of 8.3 g of itaconic anhydride and 13.2 g of 4-chlorobiphenyl is added in portions in the course of one hour. The reaction mixture is stirred at 0° C. for two hours and then added to 100 g of ice water. The solid reaction product is filtered off and washed twice with water (50 ml). After recrystallization from ethyl acetate, the product is dried at room temperature and about 100 mbar until free of solvent and water. 4-(4′-Chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid is obtained in a yield of 50% as a colorless, finely crystalline powder.

Workup

  1. additionis added in portions in the course of one hour
  2. customThe solid reaction product
  3. filtrationis filtered off
  4. washwashed twice with water (50 ml)
  5. customAfter recrystallization from ethyl acetate
  6. customthe product is dried at room temperature

Sources & evidence

ORD record
ord-a4859f2086204f9c9aacc2a3b00a1115
Source dataset
uspto-grants-2001_07
Patent number
US06265607B1

Reaction notes

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