Dichloromethane → Methyl 3-ethoxy-2'-fluorobiphenyl-4-carboxylate

HRID 531118Notes

Reaction equation

HRID 531118 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[F-].[Cs+].ClCCl.[CH2:16]([O:18][C:19]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:17]>O.COCCOC>[CH2:16]([O:18][C:19]1[CH:28]=[C:27]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:17]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 27343542-Fluorophenylboronic acidHCID 66635397Methyl 2-ethoxy-4-iodobenzoate

Product 1

HCID 90423758Methyl 3-ethoxy-2'-fluorobiphenyl-4-carboxylateYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(2-Fluorophenyl)boronic acid (0.918 g), cesium fluoride (1.99 g), and a dichloromethane adduct of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.714 g) were added to a mixture of methyl 2-ethoxy-4-iodobenzoate (1.34 g) and DME (20 mL), and the resultant mixture was stirred at 100° C. for 15 hours in an argon atmosphere. Water was added to the reaction mixture, and the mixture was filtered through celite. The filtrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.15 g).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionThe filtrate was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-64e55e28ac84454e8ed8595e3c616473
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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