Hydrochloric Acid → Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

HRID 2188946

Reaction equation

HRID 2188946 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:15]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O:13][CH3:15])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 167697291-(3-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 58762755Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

Conditions

Temperature
60 °C

Procedure

To a solution 1-(3-bromophenyl)cyclopropanecarboxylic acid (530 mg, 2.2 mmol) in methanol (5 mL) was added HCl (2.0 M in Et2O, 0.5 mL). The mixture was heated at 60° C. overnight. The solvent was evaporated and water (10 mL) was added to the residue. The mixture was neutralized with saturated NaHCO3 solution until pH 7-8. The mixture was extracted with CH2Cl2 (10 mL×2). The combined organics were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford methyl 1-(3-bromophenyl)cyclopropanecarboxylate (530 mg), which was used without further purification. ESI-MS m/z 255/257 (M+1)+. Retention time 1.68 minutes.

Workup

  1. customThe solvent was evaporated
  2. additionwater (10 mL) was added to the residue
  3. extractionThe mixture was extracted with CH2Cl2 (10 mL×2)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1322488917642a2b84234f1396dd025
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Linked notes

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