1,2-Dibromo-4,5-difluorobenzene → 1-(3-Chloro-4-fluorophenyl)-4,5-difluoro-2-[4-(methylthio)phenyl]benzene

Reaction equation

Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1Br.[CH3:11][S:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[F:29]>>[Cl:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[C:16]2[CH:17]=[CH:18][C:13]([S:12][CH3:11])=[CH:14][CH:15]=2)[CH:26]=[CH:27][C:28]=1[F:29]

Participants

Reactant 3

HCID 949491,2-Dibromo-4,5-difluorobenzene

HCID 27339594-(Methylthio)phenylboronic acid

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 234513221-(3-Chloro-4-fluorophenyl)-4,5-difluoro-2-[4-(methylthio)phenyl]benzeneYield 64%

Procedure

Following the general procedure outlined in Synthetic Scheme VII, 4.1 g (15 mmol) of 1,2-dibromo-4,5-difluorobenzene, 3.0 g (18 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) and 2.9 g (16.5 mmol) of 3-chloro-4-fluorophenylboronic acid were reacted. Purification by silica gel chromatography gave 3.5 g of 1-(3-chloro-4-fluorophenyl)-4,5-difluoro-2-[4-(methylthio)phenyl]benzene as a semi-solid which was used without further purification.