Water → Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

HRID 1595256Notes

Reaction equation

HRID 1595256 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[F-].[Cs+].O>COCCOC.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>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 22043Ethyl 4-bromobenzoateHCID 25953Cesium fluorideHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 4-bromobenzoic acid, ethyl ester (23.6 g, 103 mmol), 4-methoxyphenylboronic acid (15.6 g, 103 mmol), tetrakis(triphenylphosphine)palladium (0) (2.0 g, 1.73 mmol) and powdered caesium fluoride (30.0 g, 200 mmol) in 1,2-dimethoxyethane (300 mL) is heated at 85° C. for 3 h. The mixture is then treated with water (500 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed (saturated NaCl), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by chromatography (silica gel, 5% ethyl acetate/95% cyclohexane) to 4′-methoxy-[1,1′-biphenyl]-4-carboxylic acid, ethyl ester as a colourless crystalline solid, m.p. 103-104° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts are washed (saturated NaCl)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-bbc97165d7ac4f128a035f4c588a0810
Source dataset
uspto-grants-2001_09
Patent number
US06288092B1

Reaction notes

Loading…