Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate

HRID 2240953Notes

Reaction equation

HRID 2240953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15](=[O:36])[CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[CH3:13][O:14][C:15](=[O:36])[CH:16]=[C:10]1[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 177501013-(3-Bromophenyl)cyclobutan-1-one

Product 1

HCID 59790330Methyl 2-[3-(3-bromophenyl)cyclobutylidene]acetateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-Bromo-phenyl)-cyclobutanone (2.00 g, 8.89 mmol) and Triphenyl-phosphoranylidene acetic acid methyl ester (8.33 g, 24.9 mmol) were dissolved in dichloromethane (30 mL) inside a CEM 80 ml microwave vessel. The solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C. Pressure reached a maximum of 180 PSI. Purification by column chromatography (isocratic elution; 10% diethyl ether in hexanes) afforded 2.49 gm of a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.90-3.00 (m, 1H) 3.02-3.14 (m, 1H) 3.17-3.28 (m, 1H) 3.46-3.58 (m, 1H) 3.62 (s, 3H) 3.63-3.71 (m, 1H) 5.74 (q, J=3.0 Hz, 1H) 7.27-7.35 (m, 2H) 7.39-7.43 (m, 1H) 7.50 (t, J=1.9 Hz, 1H); MS (EI) m/z 280 [M+.].

Workup

  1. customThe solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C
  2. customPurification
  3. washby column chromatography (isocratic elution; 10% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-362ce037f97d449690b3a63b663cddb5
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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