4-Bromo-2-fluorotoluene → 3-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

HRID 36297

Reaction equation

HRID 36297 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.[C:10]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11]>[Pd]>[F:9][C:4]1[CH:3]=[C:2]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:15](=[O:17])(=[O:16])[NH:14][C:10]([CH3:11])([CH3:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[CH3:8]

Participants

4

Reactant 2

HCID 1710404-Bromo-2-fluorotolueneHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Product 1

HCID 100874243-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenylYield 92%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The palladium(0)-catalyzed coupling of 4-bromo-2-fluorotoluene with 2-(N-t-butylsulfamoyl)phenylboronic acid was carried out according to the procedure of Example 76, Step F. Purification of the crude product by flash chromatography (elution with hexane-EtOAc) gave a 92% yield of the title compound as an off-white foam (TLC in 4:1 hexane-EtOAc); mass spectrum (FAB) m/e 322 (M+1)+.

Workup

  1. customPurification of the crude product
  2. washby flash chromatography (elution with hexane-EtOAc)

Sources & evidence

ORD record
ord-3d6b6f4d22314c4ab5ae4e244b8af097
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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