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

HRID 928932

Reaction equation

HRID 928932 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[OH:10].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.C(Cl)C1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+].CC([O-])(C)C.[K+].C(O[Na])(C)(C)C.S1(CCCC1)(=O)=O>C(C(C)=O)C.CC(C)=O.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C.CS(C)=O.CCOCC>[CH2:17]([O:10][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=1[F:1])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

16

Reactant 9

HCID 7498Benzyl BromideHCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 31347SulfolaneHCID 1231742,3,4-TrifluorophenolHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 833969061-(Benzyloxy)-2,3,4-trifluorobenzene

Reagents, catalysts & solvents 6

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolventHCID 12679HexamethylphosphoramideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

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.

Workup

  1. waitThe reaction proceeds for several hours
  2. custom(3-12 h, prefer 5-10 h)

Sources & evidence

ORD record
ord-7f32c74753794d89b4fd661dedd28682
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Linked notes

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