Phosgene → 2-Chloro-1-[1-(2-methoxy-phenyl)-cyclobutyl]-ethanone

HRID 720048Notes

Reaction equation

HRID 720048 reaction equation
O1C2C=CC(C3(C(O)=O)CCC3)=CC=2OC1.Cl[C:18]([Cl:20])=O.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1([C:33](O)=[O:34])[CH2:32][CH2:31][CH2:30]1>>[Cl:20][CH2:18][C:33]([C:29]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH3:21])[CH2:32][CH2:31][CH2:30]1)=[O:34]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 219019551-(2-Methoxyphenyl)cyclobutane-1-carboxylic acidHCID 219020231-(1,3-Benzodioxol-5-yl)cyclobutanecarboxylic Acid

Product 1

HCID 219020012-Chloro-1-[1-(2-methoxy-phenyl)-cyclobutyl]-ethanone

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclobutanecarboxylic acid was converted to the corresponding chloroketone following the same procedure used for the conversion of 1-(2-Methoxy-phenyl)-cyclobutanecarboxylic acid to give 2-Chloro-1-[1-(2-methoxy-phenyl)-cyclobutyl]-ethanone. 300 mg of 1-benzo[1,3]dioxol-5-yl-cyclobutanecarboxylic acid thus provided 285 mg (83%) of 1-(1-Benzo[1,3]dioxol-5-yl-cyclobutyl)-2-chloro-ethanone. Data for this chloride: 1H NMR (300 MHz, CDCl3): δ 6.7–6.85 (m, 3H), 5.98 (s, 2H), 4.03 (s, 2H), 2.75–2.85 (m, 2H), 2.35–2.45 (m, 2H), 1.85–2.0 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 201.9, 148.6, 147.1, 135.8, 119.8, 108.9, 107.0, 101.6, 57.7, 45.4, 31.2, 16.2.

Sources & evidence

ORD record
ord-782f8cfc8b6149ee903aee8074c9cfed
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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