Sodium Carbonate → HCID 86723235, compound

HRID 1846009Notes

Reaction equation

HRID 1846009 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1.[Br:22][C:23]1[CH:24]=[CH:25][C:26]([F:30])=[C:27](I)[CH:28]=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>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([F:30])=[C:25]([C:4]2[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:8][C:3]=2[O:2][CH3:1])[CH:24]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 86723236HCID 86723236, compound

Product 1

HCID 86723235HCID 86723235, compoundYield 71%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
110 °C

Procedure

A solution of 2-(2-methoxy-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 16, 3.04 g, 9.74 mmol), 5-bromo-2-fluoro-iodobenzene (2.66 g, 8.85 mmol), and Na2CO3 (2.80, 26.55 mmol) in dioxane (60 mL) and water (15 mL) was degassed, tetrakis(triphenylphosphine)palladium(0) was added and the reaction mixture was degassed again. The reaction mixture was heated at 110° C. for 3 hours before cooling to room temperature and concentrating under reduced pressure. The residue was partitioned between water (100 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous layer was re-extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude. The crude was purified by silica gel column chromatography eluting with 10-30% EtOAc/heptane to afford the title compound in 71% yield, 2.25 g.

Workup

  1. customthe reaction mixture was degassed again
  2. temperaturebefore cooling to room temperature
  3. concentrationconcentrating under reduced pressure
  4. customThe residue was partitioned between water (100 mL) and EtOAc (100 mL)
  5. customThe organic phase was separated
  6. extractionthe aqueous layer was re-extracted with EtOAc (2×100 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude
  11. customThe crude was purified by silica gel column chromatography
  12. washeluting with 10-30% EtOAc/heptane

Sources & evidence

ORD record
ord-cb9fcf4dac304be5ba7c1bdade4455d8
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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