Iodine → Methyl 2',4'-difluoro-5'-iodo-2-methylbiphenyl-4-carboxylate

HRID 607055Notes

Reaction equation

HRID 607055 reaction equation
N[C:2]1[C:3]([F:20])=[CH:4][C:5]([F:19])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=2[CH3:18])[CH:7]=1.N(OCCC(C)C)=O.[I:29]I>C(Cl)(Cl)Cl>[F:19][C:5]1[CH:4]=[C:3]([F:20])[C:2]([I:29])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=1[CH3:18]

Participants

5

Reactant 3

HCID 807IodineHCID 8053Isoamyl NitriteHCID 57704793Methyl 5'-amino-2',4'-difluoro-2-methylbiphenyl-4-carboxylate

Product 1

HCID 57704766Methyl 2',4'-difluoro-5'-iodo-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 5′-amino-2′,4′-difluoro-2-methylbiphenyl-4-carboxylate (STEP A, 500 mg, 1.80 mmol), 3-methylbutyl nitrite (317 mg, 2.71 mmol), iodine (549 mg, 2.16 mmol) and chloroform (15 ml) were refluxed in an oil bath for 5 hours then allowed to cooled to ambient overnight. Reaction crude was purified by flash chromatography (SiO2, Biotage 40+M cartridge) eluted with a EtOAc/hexanes gradient mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=387.98; found=388.92 (M+1)+.

Workup

  1. temperatureto cooled to ambient overnight
  2. customReaction crude
  3. customwas purified by flash chromatography (SiO2, Biotage 40+M cartridge)
  4. washeluted with a EtOAc/hexanes gradient mixture
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-938a44bb62a249a198ad5775687ac102
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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