Sodium Hydroxide → 3-Trifluoromethyl-4-(2,3-dichlorophenyl)-pyrrole

HRID 247102Notes

Reaction equation

C([N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])[C:6]([C:17]([F:20])([F:19])[F:18])=[CH:5]1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[H][H]>C(OCC)C>[F:20][C:17]([F:18])([F:19])[C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[CH:8][NH:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

29.0 g of N-acetyl-4-(2,3-dichlorophenyl)-3-trifluoromethylpyrrole are dissolved in 500 ml of diethyl ether. This solution is subsequently cooled to 0° C., and to it are added portionwise 13.7 g of lithium aluminium hydride. The mixture is afterwards stirred for 1 hour, and there are then added dropwise at 5° C. 55 ml of 4% sodium hydroxide solution, in the course of which elementary hydrogen is given off, and the mixture is subsequently stirred for a further hour at room temperature. The mixture is then filtered; the filtrate is dried over magnesium sulfate, again filtered, and concentrated by evaporation. The resulting oil is distilled at 150°/8×10-5 mbar. By covering it with hexane, there is obtained from the distillate 3-trifluoromethyl-4-(2,3-dichlorophenyl)pyrrole in the form of colourless crystals, m.p. 63°-65° C.

Workup

additionthere are then added dropwise at 5° C
stirringthe mixture is subsequently stirred for a further hour at room temperature
filtrationThe mixture is then filtered
dry with materialthe filtrate is dried over magnesium sulfate
filtrationagain filtered
concentrationconcentrated by evaporation
distillationThe resulting oil is distilled at 150°/8×10-5 mbar

Sources & evidence

ORD record: ord-13d8665e720342c48454fb148bce99bb
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705801

Reaction notes

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