Ethanol → 2-(4-Hydroxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester

HRID 62892Notes

Reaction equation

HRID 62892 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH3:17])[C:10]=1[CH3:18])=[O:5])[CH3:2].B(Br)(Br)Br.CCO.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:17])[C:10]=1[CH3:18])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 901182242-(4-Methoxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 901180052-(4-Hydroxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl esterYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Methoxy-2,3-dimethyl-phenyl)-cyclopropane carboxylic acid ethyl ester (0.32 g, 1.29 mmol) obtained in Step B was dissolved in DCM (5 mL), and the reactant was cooled to 0˜5° C. BBr3 solution (3.90 mL, 3.87 mmol, 1M/DCM) was added dropwise thereto, and the mixture was stirred at 0˜5° C. for 2 hours. After the termination of the reaction, EtOH and saturated sodium bicarbonate solution were added thereto in turn, and the mixture was stirred. The separated organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.24 g, 79%).

Workup

  1. temperaturethe reactant was cooled to 0˜5° C
  2. additionwere added
  3. stirringin turn, and the mixture was stirred
  4. concentrationThe separated organic layer was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-f14a97a08abe4d9d95ff15ad7ee75b70
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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