Potassium Carbonate → 4,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl

HRID 547847Notes

Reaction equation

HRID 547847 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[C:18]([F:19])=[CH:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[C:15]([O:27][CH3:28])[CH:14]=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[C:18]([F:19])=[CH:17][C:16]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=3)=[CH:24][CH:25]=2)=[C:15]([O:27][CH3:28])[CH:14]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-olHCID 582877952,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenyl

Product 1

HCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenylYield 39.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromomethyl-3-nitro-benzene (455 mg, 2.11 mmol), 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol (0.5 g, 2.11 mmol), and dried, finely ground potassium carbonate (363 mg, 2.63 mmol) in 30 mL acetone were refluxed under argon for 16 hrs similar to 2,4-difluoro-4′-(3-nitro-benzyloxy)-biphenyl above. The crude product was purified by trituration with 5% ethyl acetate in hexanes to yield 0.31 g (38%) of 4,5-difluoro-2-methoxy-4′-(3-nitro-benzyloxy)-biphenyl. LC-MS (ES) calculated for C20H15F2NO4, 371.34; found m/z 370 [M−H]−.

Workup

  1. customThe crude product was purified by trituration with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7843d6c1e9c34da1b7cdb13f12fc4d3c
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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