Potassium Carbonate → 3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoic acid methyl ester

HRID 1665235Notes

Reaction equation

HRID 1665235 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]1[C:32]([F:33])=[CH:31][C:30](B(O)O)=[C:29]([O:37][CH3:38])[CH:28]=1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:30]3[CH:31]=[C:32]([F:33])[C:27]([F:26])=[CH:28][C:29]=3[O:37][CH3:38])=[CH:14][CH:13]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate

Product 1

HCID 671503803-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoic acid methyl esterYield 95.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Bis(tricyclohexylphosphine)palladium (236 mg, 0.35 mmol) was added to a stirred solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (6.5 g, 17.73 mmol), potassium carbonate (3.67 g, 26.6 mmol) and 4,5-difluoro-2-methoxyphenylboronic acid (5 g, 26.6 mmol) in 156 ml, dioxane were reacted as above and purified by flash chromatography with a gradient of 0-5% ethyl acetate in hexanes to give 6.51 g (95.6%) of 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoic acid methyl ester.

Workup

  1. customwere reacted as above and
  2. custompurified by flash chromatography with a gradient of 0-5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0151aaf89d214cf787b2d68ec24b2baf
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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