Hydrochloric Acid → 3-(4-Bromobenzoyl)propionic acid

HRID 82746

Reaction equation

HRID 82746 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1.Cl>ClCCl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 7961BromobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 806463-(4-Bromobenzoyl)propionic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous aluminum trichloride (29.1 g, 218 mmol) was suspended in dichloromethane (120 mL) and cooled to 0° C. Bromobenzene (35.1 g, 224 mmol) was added carefully. When the addition was complete, succinic anhydride (10.0 g, 100 mmol) was added in ten portions carefully. Then the mixture was warmed to room temperature and stirred for 4 h. TLC showed the reaction was complete, 6N HCl (50 mL) was added dropwise. The solid was filtered, washed with distilled water (10 mL×2) and dried in vacuo to afford A-1 as a white solid (22 g, yield 82%).

Workup

  1. additionWhen the addition
  2. temperatureThen the mixture was warmed to room temperature
  3. filtrationThe solid was filtered
  4. washwashed with distilled water (10 mL×2)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d3a34d3823be4c5db6e84a2dd561fe86
Source dataset
uspto-grants-2014_09
Patent number
US08846736B2

Linked notes

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