Toluene → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

HRID 51964

Reaction equation

C1(C)C=CC=CC=1.[F:8][C:9]([F:26])([F:25])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22](O)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1.S(Cl)([Cl:29])=O>CN(C=O)C>[F:8][C:9]([F:26])([F:25])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([Cl:29])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a nitrogen purged 3 liter 4-neck flask fitted with a condenser, mechanical stirrer, temperature probe, and connected to a 2M aqueous NaOH scrubber was added toluene (1 L), 4′-trifluoromethyl-biphenyl-2-carboxylic acid (250 g, 0.94 mol, 1 equiv), and DMF (5 mL). 4′-Trifluoromethyl-biphenyl-2-carboxylic acid can be obtained from Aldrich, Milwaukee, Wis. The solution was heated to 60° C. and thionyl chloride (110 mL, 1.5 mol, 1.6 equiv) was added at such a rate as to maintain the temperature below 65° C. The addition was complete after 30 minutes and the reaction was heated to reflux. After 4 hours, the heating was stopped and the reaction was allowed to stir overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was used in the next step without further purification. The material crystallized to a solid at room temperature.

Workup

customTo a nitrogen purged 3 liter 4-neck flask
customfitted with a condenser, mechanical stirrer
temperatureto maintain the temperature below 65° C
additionThe addition
temperaturethe reaction was heated to reflux
waitAfter 4 hours
concentrationThe reaction mixture was concentrated in vacuo
customthe residue was used in the next step without further purification
customThe material crystallized to a solid at room temperature

Sources & evidence

ORD record: ord-b541533d9a334318badf7770b41c8ee0
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713489B2

Linked notes

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