Sodium Carbonate → 4'-Benzyloxy-biphenyl-3-carboxylic acid ethyl ester

HRID 2261763Notes

Reaction equation

HRID 2261763 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](I)[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>COCCOC.C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:28][CH:29]=2)[CH:8]=[CH:9][CH:10]=1)=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 143542Ethyl 3-iodobenzoateHCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 675281234'-Benzyloxy-biphenyl-3-carboxylic acid ethyl esterYield 76.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl-3-iodobenzoate (2.5 g, 1 equiv) in ethylene glycol dimethyl ether (20 mL) are added 2 M sodium carbonate solution (40 mL), 4-benzyloxybenzene boronic acid (2.5 g, 1.2 equiv) and tetrakistriphenylphosphine palladium(0) (1.05 g, 0.1 equiv). The reaction mixture is heated to reflux for 2 h. The reaction mixture is allowed to cool to room temperature and is diluted with 300 mL 50% sodium bicarbonate solution. The product is extracted three times with methylene chloride. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with ethyl acetate/hexanes (2:98 to 8:92) to give the desired product (2.3 g, 76%) as a white solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2 h
  3. extractionThe product is extracted three times with methylene chloride
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified via flash chromatography
  8. washeluting with ethyl acetate/hexanes (2:98 to 8:92)

Sources & evidence

ORD record
ord-df9b38b5cc864b23ae25159ac416a560
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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