Ethyl chloroformate → Ethyl 2,6-dichloro-4-(trifluoromethyl)benzoate

HRID 266530Notes

Reaction equation

C([Li])CCC.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1Br.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].[Cl-].[NH4+]>CCOCC>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (1.6M in hexane, 330 ml) was added dropwise with stirring to a solution of 2,6-dichloro-4-trifluoromethylbromobenzene (163.3 g) in ether while maintaining the temperature below -70° C. The mixture was stirred for 1 hour at -78° C. then ethyl chloroformate (61.7 g) was added while maintaining the temperature below -70° C. The mixture was stirred at room temperature overnight. It was cooled to 0° C. and a saturated aqueous solution of ammonium chloride was added. The layers were separated and the organic layer was washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give ethyl 2,6-dichloro-4-trifluoromethylbenzoate (123.9 g) as a colourless liquid bp 90°-96° C. at 5 mmHg.

Workup

temperaturewhile maintaining the temperature below -70° C
temperaturewhile maintaining the temperature below -70° C
stirringThe mixture was stirred at room temperature overnight
temperatureIt was cooled to 0° C.
customThe layers were separated
washthe organic layer was washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
distillationthe residue was distilled

Sources & evidence

ORD record: ord-32a9205cdedc41cfbe84b2a300538bba
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650533

Reaction notes

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