Acetic Acid → Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

HRID 861025Notes

Reaction equation

HRID 861025 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].C[C:16](O)=[O:17]>CCO.[Cl-].[Na+].O>[CH3:16][O:17][C:11]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)=[O:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Product 1

HCID 46739795Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of -(4-bromo-phenyl)-cyclopropanecarbonitrile from Step 1 in EtOH (0.2M) was added NaOH 25% (10 eq.). The mixture was stirred for 6 h at 100° C., quenched with AcOH (20 eq.), poured in brine, extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was dissolved in CH2Cl2 and diazomethane was added portionwise until the esterification was completed by TLC. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as a colorless oil.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. additiondiazomethane was added portionwise until the esterification

Sources & evidence

ORD record
ord-b49024aea32b4a2eb2534955fd7ceac2
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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