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

HRID 1442811Notes

Reaction equation

HRID 1442811 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.Cl.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 4

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

Product 1

HCID 806463-(4-Bromobenzoyl)propionic acidYield 62.2%

Conditions

Temperature
-10 °C

Procedure

AlCl3 (26.7 g, 0.200 mol) was added in one portion to a stirred mixture of succinic anhydride (10.0 g, 0.100 mol) in bromobenzene (97.0 g) at −10° C. under N2 atmosphere. The reaction temperature was maintained at −10° C. for 1Hour and was then allowed to warm to room temperature. The mixture was stirred at room temperature overnight and poured into ice water. HCl (1M) was added slowly until pH 5. The mixture was extracted with ethyl acetate (150 mL×2). The combined organics were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was washed with ether to afford 4-(4-bromophenyl)-4-oxobutanoic acid (16.0 g, 62%) as a white solid. 1H NMR (300 MHz, DMSO) δ 12.15 (br s, 1H), 7.90 (d, J=8.7, 2H), 7.73 (d, J=8.7, 2H), 3.22 (t, J=6.0, 2H), 2.55 (t, J=6.0, 2H).

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (150 mL×2)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-dc92ebc659ec421bb2fb6c703c277da1
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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