Cesium carbonate → 3-(4-Ethoxycarbonylphenyl)benzoic acid

HRID 1678453Notes

Reaction equation

HRID 1678453 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:11]([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:11]([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)=[CH:18][CH:17]=1)=[O:15])[CH3:12]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 114563-Bromobenzoic acidHCID 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 532184123-(4-Ethoxycarbonylphenyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromo-benzoic acid (4.02 g) and 4-ethoxycarbonyl-phenyl boronic acid (3.88 g) in DME (100 ml) containing cesium carbonate (6.5 g) and tetrakis(triphenylphosphine) palladium (0) (1.15 g) was heated to reflux for 24 h. The cooled mixture was then filtered through celite and evaporated giving the crude title compound as a white solid which was used without purification in the next synthetic step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. filtrationThe cooled mixture was then filtered through celite
  4. customevaporated

Sources & evidence

ORD record
ord-d5238a6e199d4a32b8cfc58a6a66ace1
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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