Diazomethane → Methyl (1S,2S)-2-(4-Bromophenyl)cyclopropanecarboxylate

HRID 718684

Reaction equation

HRID 718684 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[N+](=[CH2:16])=[N-]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:16][C@@H:9]2[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 816774Methyl 4-bromocinnamate

Product 1

HCID 117728321Methyl (1S,2S)-2-(4-Bromophenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of compound 66c (1.50 g, 6.22 mmol) and Pd(OAc)2 (90 mg, 0.40 mmol) in DCM (20 mL) was added an ethereal solution of compound 66b (200 mL). After stirring for 10 min at 0° C., the reaction mixture was concentrated under reduced pressure to yield a residue, which was subjected to flash column chromatography on silica gel (10% EtOAc/petroleum ether) to afford compound 66d as colorless oil. Mass Spectrum (GCMS, ESI pos.): Calcd. for C11H11BrO2: 254.0 (M). found: 254.0.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto yield a residue, which

Sources & evidence

ORD record
ord-899384643d394dd09ce1f98e8bfb819a
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Linked notes

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