Potassium Carbonate → HCID 23451096, compound

HRID 1839953Notes

Reaction equation

HRID 1839953 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](S(C(F)(F)F)(=O)=O)[C:5]([S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[CH:4][C:3]=1[Cl:22].[CH3:23][S:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.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:3]1[CH:4]=[C:5]([S:15]([C:18]([F:19])([F:20])[F:21])(=[O:16])=[O:17])[C:6]([C:28]2[CH:29]=[CH:30][C:25]([S:24][CH3:23])=[CH:26][CH:27]=2)=[CH:7][C:2]=1[Cl:1]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 23450940HCID 23450940, compound

Product 1

HCID 23451096HCID 23451096, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, 5 g (4.3 mmol) of Pd(PPh3)4 was added to a stirred solution of 7.9 g (17.8 mmol) of 1,2-dichloro-4,5-bis(trifluoromethanesulfonyl)benzene (Step 4), 3.0 g (18 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) and 7.4 g (54 mmol) of anhydrous K2CO3 powder in 90 mL of toluene. The reaction was stirred at reflux for 48 hours, and diluted with CH2Cl2. The resulting solution was washed with water and brine, and dried over MgSO4. Purification by silica gel plug with ethyl acetate/hexane (5:95 to 30:70) gave 4.8 g (56%) of 1,2-dichloro-4-[4-(methylthio)phenyl]-5-(trifluoromethanesulfonyl)benzene as a colorless solid: NMR (CDCl3) δ 2.54 (s, 3H), 7.33 (s, 4H), 7.50 (S, 1H), 7.56 (S, 1H).

Workup

  1. temperatureat reflux for 48 hours
  2. washThe resulting solution was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customPurification by silica gel plug with ethyl acetate/hexane (5:95 to 30:70)

Sources & evidence

ORD record
ord-17bde6e432de49acbdce4f3d0478000e
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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