Hydrochloric Acid → 1-(4-(Benzyloxy)phenyl)-2,2,2-trifluoroethanone

HRID 1419797Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:21][C:22]([F:28])([F:27])[C:23](OC)=[O:24].Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:23](=[O:24])[C:22]([F:28])([F:27])[F:21])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of 91.2 ml (0.23 mol) of 2.5M n-butyllithium solution was added dropwise at -40° C. to a solution of 50.0 g (0.19 mol) of 4-bromophenol benzyl ether in 250 ml of tetrahydrofuran. The mixture was subsequently stirred for a short time at -40° C., then cooled to -78° C., and 34 g (0.27 mol) of methyl trifluoroacetate were added dropwise. The mixture was allowed to come to room temperature and then stirred at 0° C. for 3 hours. For working up, 120 ml of dilute hydrochloric acid were added dropwise, the mixture was diluted with toluene, and the organic phase was separated off, washed with water, dried and concentrated. A brown solid was obtained which was recrystallized from petroleum ether/ethyl acetate 10:1.

Workup

temperaturecooled to -78° C.
customto come to room temperature
stirringstirred at 0° C. for 3 hours
customthe organic phase was separated off
washwashed with water
customdried
concentrationconcentrated
customA brown solid was obtained which
customwas recrystallized from petroleum ether/ethyl acetate 10:1

Sources & evidence

ORD record: ord-a7ad61a6a6274741936626cbae8e0810
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889012

Reaction notes

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