Hydrochloric Acid → Methyl 1-(2-bromophenyl)cyclopropane-1-carboxylate

HRID 592339Notes

Reaction equation

HRID 592339 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]1.Cl.[CH3:15]O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]([O:13][CH3:15])=[O:12])[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 200261761-(2-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 75486174Methyl 1-(2-bromophenyl)cyclopropane-1-carboxylate

Procedure

A solution of 1-(2-bromophenyl)cyclopropanecarboxylic acid (500 mg, 2.07 mmol) in MeOH (10 mL) was treated with a solution of concentrated aqueous HCl (0.5 mL). The resulting mixture was stirred for 16 hours at room temperature and then heated to reflux and stirred for a further 24 hours. The volatiles were evaporated and the residue was dissolved in EtOAc. The organic layer was washed with saturated solution of NaHCO3, brine and then dried over MgSO4. The solvent was removed in vacuo to give the title compound I4 (400 mg, 76%) as an orange oil; 1H NMR (400 MHz, CDCl3) δ 7.60-7.54 (m, 1H), 7.32-7.24 (m, 2H), 7.15 (m, 1H), 3.63 (s, 3H), 1.75 (d, J=3.1 Hz, 2H), 1.21 (q, J=4.0 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for a further 24 hours
  4. customThe volatiles were evaporated
  5. dissolutionthe residue was dissolved in EtOAc
  6. washThe organic layer was washed with saturated solution of NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fe87c54770aa4f6a8b8fb4d335a913c0
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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