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

HRID 1288716Notes

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-825cef61c5cc4ab9a371de940b3a9004
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747424

Reaction notes

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