Triethylamine → Dimethyl 2'-methoxybiphenyl-3,5-dicarboxylate

HRID 2071139Notes

Reaction equation

HRID 2071139 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>CC(O)C.O.CCOCC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 59569648Dimethyl 2'-methoxybiphenyl-3,5-dicarboxylate

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To dimethyl 5-bromoisophthalate (1.5 g, 5.5 mmol, Aldrich) in i-PrOH (33.3 ml) and water (16.7 ml), 2-methoxy phenyl boronic acid (Aldrich), triethyl amine (841 mg, 8.25 mmol) and PdCl2(dppf) (180 mg, 0.22 mmol) were added and the reaction mixture was refluxed for 4 h. Then reaction mixture was diluted with ether, washed with water, brine and dried. Volatiles were removed under vacuum and the crude residue was column chromatographed (30% ethylacetate/70% hexanes) to yield 650 mg of dimethyl 2′-methoxybiphenyl-3,5-dicarboxylate as white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. customThen reaction mixture
  3. washwashed with water, brine
  4. customdried
  5. customVolatiles were removed under vacuum
  6. customchromatographed (30% ethylacetate/70% hexanes)

Sources & evidence

ORD record
ord-82a3e1f01ecb4aeab26c1836fa42792e
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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