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

HRID 1530814Notes

Reaction equation

HRID 1530814 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-].[NH4+].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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9893Methyl trifluoroacetateHCID 25517Ammonium ChlorideHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 212526911-(4-(Benzyloxy)phenyl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., 182.4 ml of a 2.5 M butyllithium solution were added dropwise to a solution of 100 g of 4-benzyloxy-1-bromobenzene in 500 ml of dry tetrahydrofuran. Stirring was continued at −78° C. for 15 min, and 68.0 g of methyl trifluoroacetate were then added dropwise at this temperature. Stirring was subsequently continued at −20° C. for 2 hours. For work-up, 80 ml of saturated aqueous ammonium chloride were added dropwise, the mixture was mixed with 250 ml of dilute hydrochloric acid and diluted with 500 ml of toluene, and the organic phase was washed with water, dried and concentrated, to give the title product as a colourless oil which crystallised on digestion with heptane.

Workup

  1. stirringStirring
  2. waitwas subsequently continued at −20° C. for 2 hours
  3. washthe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3219198d51574108bd13d30f16e4b80f
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

Loading…