Cesium carbonate → Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylate

HRID 494194

Reaction equation

HRID 494194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=2[OH:18])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:25][O:26][CH2:27][CH2:28]Br>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=2[O:18][CH2:28][CH2:27][O:26][CH3:25])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 69037981[1,1'-Biphenyl]-4-carboxylic acid, 4'-fluoro-2-hydroxy-, methyl ester

Product 1

HCID 69039439Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of methyl 4′-fluoro-2-hydroxy-1,1′-biphenyl-4-carboxylate (D75) (400 mg, 1.6 mmol) in DMF (10 ml) was added cesium carbonate (1.27 g, 3.9 mmol) and 2-methoxyethylbromide (400 mg, 1.6 mmol) and the reaction was heated at 80° C. overnight. The solvent was evaporated and the residue was dissolved in EtOAc, washed with water and brine, then dried over MgSO4 to give the title compound (494 mg) which was used without further purification in the next step. MS(ES): (M-MeOH)H+ 273.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-833d51aee49b4b84b114c243563ce9ec
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Linked notes

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