Cesium carbonate → Ethyl 4'-(methoxymethyl)biphenyl-4-carboxylate

HRID 1519668Notes

Reaction equation

HRID 1519668 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 598822262-(4-(Methoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 71268182Ethyl 4'-(methoxymethyl)biphenyl-4-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-iodobenzoate (5.5 g), tetrakis(triphenylphosphine)palladium (1.2 g), and cesium carbonate (9.8 g) were added to an ethanol (0.10 L) solution of 2-[4-(methoxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.1 g), as obtained in Example 3-(1). The mixture was stirred for 30 minutes at 80° C., and then the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=85/15) to obtain ethyl 4′-(methoxymethyl)biphenyl-4-carboxylate (light yellow solid) (3.5 g, 80%).

Workup

  1. customas obtained in Example 3-(1)
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by OH type silica gel chromatography (hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-fa2607e59d684a96b4cec56c32b6e193
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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