Sodium Carbonate → HCID 86723255, compound

HRID 1846031Notes

Reaction equation

HRID 1846031 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](I)[CH:3]=1.[CH2:10]([S:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH3:11].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH2:10]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=2[F:8])=[CH:17][CH:16]=1)(=[O:13])=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27734204-(Ethylsulphonyl)benzeneboronic acidHCID 27827504-Bromo-1-fluoro-2-iodobenzene

Product 1

HCID 86723255HCID 86723255, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed, room temperature solution of 4-bromo-1-fluoro-2-iodobenzene (2.80 g, 9.30 mmol) and 4-(ethylsulphonyl)benzeneboronic acid (2.27 g, 10.6 mmol), in anhydrous 1,4-dioxane (120 mL) was added aqueous Na2CO3 solution (1M, 46.5 mL, 46.5 mmol) followed by the tetrakistriphenylphosphine palladium(0) (537 mg, 0.465 mmol). The slightly yellow solution was degassed 3 times by vacuum/nitrogen refill then was heated to 100° C. with stirring for 2 hours. The reaction mixture was cooled then suspended in CH2Cl2 (50 mL) and filtered through a pad of celite. The pad was rinsed well with CH2Cl2 (100 mL) and the filtrate was washed with water (2×50 mL) then dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to give crude product as a yellow oil. Purification by silica gel column chromatography eluting with heptane:EtOAc 1:1 afforded the title compound as a colourless oil in 84% yield, 2.696 g.

Workup

  1. customThe slightly yellow solution was degassed 3 times by vacuum/nitrogen refill
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through a pad of celite
  4. washThe pad was rinsed well with CH2Cl2 (100 mL)
  5. washthe filtrate was washed with water (2×50 mL)
  6. dry with materialthen dried over anhydrous MgSO4 (s)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give crude product as a yellow oil
  10. customPurification by silica gel column chromatography
  11. washeluting with heptane:EtOAc 1:1

Sources & evidence

ORD record
ord-6a55fe7a2f2240dba188f261c77b2c87
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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