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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928932Generated: October 26, 2026

Benzyl Bromide → 1-(Benzyloxy)-2,3,4-trifluorobenzene

https://huagongshe.com/reaction/928932

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzyl BromideHCID 7498—
ReactantBenzyl ChlorideHCID 7503—
ReactantSodium CarbonateHCID 10340—
ReactantPotassium CarbonateHCID 11430—
ReactantSulfolaneHCID 31347—
Reactant2,3,4-TrifluorophenolHCID 123174—
ReactantSodium BicarbonateHCID 516892—
ReactantPotassium tert-butoxideHCID 23665647—
Reactantsodium 2-methylpropan-2-olateHCID 178418730—
SolventAcetoneHCID 180—
SolventDimethyl SulfoxideHCID 679—
SolventDiethyl EtherHCID 3283—
SolventMethyl Ethyl KetoneHCID 6569—
SolventHexamethylphosphoramideHCID 12679—
Solvent2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 81646—
Product1-(Benzyloxy)-2,3,4-trifluorobenzeneHCID 83396906—

Reaction Steps

2,3,4-Trifluorophenol was protected with hydroxy protection reagent (examples include BnBr, BnCl) at ambient temperature in the presence of base (include Na2CO3, K2CO3, NaHCO3, KHCO3, t-BuOK, t-BuONa) in appropriate inert solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer acetone and methyl ethyl ketone). The reaction proceeds for several hours (3-12 h, prefer 5-10 h). 1-(Benzyloxy)-2,3,4-trifluorobenzene is obtained after conventional workup.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290468B2
Source datasetuspto-grants-2016_03
ORD IDord-7f32c74753794d89b4fd661dedd28682
Source noteuspto-grants-2016_03