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

HRID 547855Notes

Reaction equation

HRID 547855 reaction equation
CN(C=O)C.Br[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1.[F:17][C:18]1[C:23]([F:24])=[CH:22][C:21]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:20]([O:32][CH3:33])[CH:19]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C(OCC)(=O)C>[F:17][C:18]1[C:23]([F:24])=[CH:22][C:21]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=3)=[CH:29][CH:30]=2)=[C:20]([O:32][CH3:33])[CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 2733832Lithium HexamethyldisilazideHCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-ol

Product 1

HCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenylYield 96.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of DMF (5 ml), 1-bromomethyl-3-nitro-benzene (0.92 g, 4.2 mmol), and 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol (1 g, 4.2 mmol) was added lithium bis(trimethylsilyl)amide (1M in THF, 4.4 ml). The reaction was stirred at room temperature overnight and was then diluted with ethyl acetate (200 mL), washed with water (200 mL), aqueous ammonium chloride (10%, 200 mL) and brine, dried over magnesium sulfate and concentrated to yield 4,5-difluoro-2-methoxy-4′-(3-nitro-benzyloxy)-biphenyl as yellow solid (1.5 g, 95%). LC-MS (ES) calculated for C20H15F2NO4, 371.1; found m/z 370 [M−H]−.

Workup

  1. washwashed with water (200 mL), aqueous ammonium chloride (10%, 200 mL) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c20ab3bb1f724881b211dcb3746ed574
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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