Thionyl Chloride → 4-[(4-Butylphenyl)ethynyl]benzoyl chloride

HRID 551982Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([Cl:24])=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4-butylphenylethynyl)benzoic acid (300 mg; 1.08 mmol) in anhydrous toluene (10 mL) was added thionyl chloride (0.39 ml; 5.39 mmol). The reaction mixture was stirred overnight at 60° C. under N2 atmosphere. The solvent and thionyl chloride were removed under reduced pressure to give 296 mg of the title compound as a green solid. 1H NMR (CDCl3) δ: 8.09 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 2.64 (t, J=8.7 Hz, 2H), 1.61 (q, J=7.6 Hz, 2H), 1.37 (q, J=7.8 Hz, 2H), 0.93 (t, J=7.3 Hz, 3H).

Workup

customThe solvent and thionyl chloride were removed under reduced pressure

Sources & evidence

ORD record: ord-331343361b214964b982b27c062fed82
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

Loading…