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

HRID 2359981Notes

Reaction equation

HRID 2359981 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-9b241ebf8eb74173a751b418c52d0654
Source dataset
uspto-grants-2014_04
Patent number
US08686015B2

Reaction notes

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