Sodium Carbonate → HCID 86723271, compound

HRID 1846050Notes

Reaction equation

HRID 1846050 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([F:21])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25](I)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[C:27]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[F:21])[CH:28]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27736524-Chloro-1-fluoro-2-iodobenzeneHCID 86723254HCID 86723254, compound

Product 1

HCID 86723271HCID 86723271, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-(4-(ethylsulfonyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 45, 1.77 g, 5.64 mmol), 4-chloro-1-fluoro-2-iodobenzene (1.28 g, 5.00 mmol), and sodium carbonate (1.59 g, 15.00 mmol) in dioxane (40 mL) and water (10 mL) was degassed. Tetrakis(triphenylphosphine)palladium(0) (577 mg, 0.50 mmol) was added and the mixture was degassed twice more, and the reaction warmed to 80° C. for 2 hours. The reaction was cooled and diluted with EtOAc (50 mL) and water (50 mL), the layers separated and the aqueous extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 and the solvent removed in vacuo. The crude was purified by silica gel column chromatography eluting with EtOAc:heptane 1:19 to 1:1 to give the title compound as a colourless oil 28% yield, 443 mg.

Workup

  1. customthe mixture was degassed twice more
  2. temperatureThe reaction was cooled
  3. additiondiluted with EtOAc (50 mL) and water (50 mL)
  4. customthe layers separated
  5. extractionthe aqueous extracted with EtOAc (2×30 mL)
  6. washThe combined organic layers were washed with brine (30 mL)
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe crude was purified by silica gel column chromatography
  10. washeluting with EtOAc:heptane 1:19 to 1:1

Sources & evidence

ORD record
ord-0e80d6acb98e43b5ba37d15383f7a503
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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