Triethylamine → 1-Chloro-4-{1-[(E)-2-nitroethenyl]cyclobutyl}benzene

HRID 591188

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12](O)[CH2:13][N+:14]([O-:16])=[O:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(/[CH:12]=[CH:13]/[N+:14]([O-:16])=[O:15])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(1-(4-Chlorophenyl)cyclobutyl)-2-nitroethanol (5.2 g, 20.34 mmol) was dissolved in dichloromethane (41 ml) and trifluoroacetic acid anhydride (2.87 ml, 20.34 mmol) was added. The reaction mixture was cooled to 0° C. and triethylamine (5.67 ml, 40.7 mmol) was added dropwise. The reaction was slowly warmed to room temperature and stirring was continued for 2 h. The reaction mixture was diluted with dichloromethane and washed with aqueous hydrochloric acid (1 N). The organic layer was dried (magnesium sulfate) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 3.99 g (16.79 mmol, 83%)

Workup

temperatureThe reaction was slowly warmed to room temperature
washwashed with aqueous hydrochloric acid (1 N)
dry with materialThe organic layer was dried (magnesium sulfate)
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record: ord-03889bf11f594b80b3e878bbe1e774b0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238619B2

Linked notes

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