Hydrochloric Acid → cis-2-(4-Bromobenzoyl)cyclopropanecarboxylic acid

HRID 9541Notes

Reaction equation

HRID 9541 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH:12]12[CH2:17][CH:16]1[C:15](=[O:18])[O:14][C:13]2=[O:19].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]([C@H:16]2[CH2:17][C@H:12]2[C:13]([OH:19])=[O:14])=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67147316cis-2-(4-Bromobenzoyl)cyclopropanecarboxylic acidYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) stirred solution of bromobenzene (9.09 g, 57.89 mmol) and AlCl3 (18.36 g, 137.84 mmol) in dry DCM (150 mL) was added 3-oxabicyclo[3.1.0]hexane-2,4-dione (5.40 g, 48.24 mmol). The reaction mixture was stirred at rt for 3 days. The dark-red solution was then poured into ice-cold water (120 mL), and conc. HCl (10 mL) was added. The solution was stirred for few minutes, and the layers were separated. The aqueous layer was extracted with DCM and the combined organic phases were washed with water, brine, dried over Na2SO4 and concentrated to give cis-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.69 g, 65%). LC-MS ret. time 2.50; m/z 270 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.54 (m, 1H), 1.85 (m, 1H), 2.37 (m, 1H), 2.88 (m, 1H), 7.65 (m, 2H), 7.90 (m, 2H).

Workup

  1. additionwas added
  2. stirringThe solution was stirred for few minutes
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with DCM
  5. washthe combined organic phases were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f34df0009af4ec5b9397ec1a5edea37
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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