2-Bromo-5-(trifluoromethyl)benzenamine → 1-Bromo-2-iodo-4-(trifluoromethyl)benzene

HRID 1171935Notes

Reaction equation

HRID 1171935 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1N.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[I:24].[PH:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>Cl[Si](C)(C)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][C:15]=1[I:24].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:20]([P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])([F:22])[F:23]

Participants

6

Reactant 3

HCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzeneHCID 178476833HCID 178476833, compound

Product 2

HCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzeneHCID 86621243Diethyl [2-bromo-5-(trifluoromethyl)phenyl]difluoromethylphosphonate

Reagents, catalysts & solvents 1

HCID 6397ChlorotrimethylsilaneCatalyst

Procedure

2-Bromo-5-(trifluoromethyl)-iodobenzene was synthesized from 2-bromo-5-(trifluoromethyl)benzeneamine according to the procedure described for Example 86. Diethyl [2-bromo-5-(trifluoromethyl)phenyl]difluoromethylphosphonate was synthesized from 2-bromo-5-(trifluoromethyl)-iodobenzene according to Example 25 except that chlorotrimethylsilane (several drops) was used in place of acetic acid. Compound 87 was synthesized according to procedures similar to those of Example 40 from this corresponding diethyl phosphonate. MS (ES−): m/z 353.0, 355.0 (M−H). 1H NMR: (DMSO-d6, 400 MHz) δ 7.94 (d, J=8.2, 1H), 7.90 (s, 1H), 7.68 (d, J=8.2, 1H).

Sources & evidence

ORD record
ord-22df5df8091247a7905330ca67044bdc
Source dataset
uspto-grants-2010_11
Patent number
US07829737B2

Reaction notes

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