Sodium Carbonate → HCID 86723248, compound

HRID 1846025Notes

Reaction equation

HRID 1846025 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[C:9]([O:22][CH3:23])[CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[Br:24][C:25]1[CH:26]=[CH:27][C:28]([F:32])=[C:29](I)[CH:30]=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:24][C:25]1[CH:30]=[CH:29][C:28]([F:32])=[C:27]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([CH:1]([CH3:2])[CH3:3])(=[O:5])=[O:6])=[CH:8][C:9]=2[O:22][CH3:23])[CH:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 86723249HCID 86723249, compound

Product 1

HCID 86723248HCID 86723248, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(4-(isopropylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 36, 374 mg, 1.10 mmol) and 5-bromo-2-fluoroiodobenzene (300 mg, 1.00 mmol) in dioxane (6 mL) and water (2.5 mL) was added sodium carbonate (317 mg, 3.00 mmol). The mixture was degassed with nitrogen for 20 minutes, tetrakis(triphenylphosphine)palladium(0) (58.0 mg, 0.05 mmol) was added and the reaction mixture was stirred at 100° C. under a nitrogen atmosphere for 12 hours. The cooled reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc/cyclohexane 25/75 to afford the title compound as a yellow oil in 69% yield, 0.27 g.

Workup

  1. customThe mixture was degassed with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with EtOAc/cyclohexane 25/75

Sources & evidence

ORD record
ord-d11a5e417f1b4bd896c6753776800668
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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