Potassium Carbonate → HCID 58287797, compound

HRID 547848Notes

Reaction equation

HRID 547848 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].FC1C=C(F)C=CC=1C1C=CC(OCC2C=CC=C([N+]([O-])=O)C=2)=CC=1>CC(C)=O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 582599972',4',5'-Trifluoro-biphenyl-4-olHCID 58287795HCID 58287795, compound

Product 1

HCID 58287797HCID 58287797, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromomethyl-3-nitro-benzene (0.9 g, 4.2 mmol), 2′,4′,5′-trifluoro-biphenyl-4-ol (1.15 g, 4.2 mmol), and dried, finely ground potassium carbonate (725 mg, 5.25 mmol) in 40 mL acetone were refluxed under argon for 19 hrs similar to 2,4-difluoro-4′-(3-nitro-benzyloxy)-biphenyl above. The crude product was purified by flash chromatography with 0-6% ethyl acetate in hexanes to yield 0.71 g (47%) of 2,4,5-trifluoro-4′-(3-nitro-benzyloxy)-biphenyl. LC-MS (ES) calculated for C19H12F3NO3, 359.31; found m/z 358 [M−H]−.

Workup

  1. customThe crude product was purified by flash chromatography with 0-6% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bb621bf6217e43ceb0825499943252f4
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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