Triethyl phosphite → Diethyl (2-bromo-5-iodophenyl)oxomethylphosphonate
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.BrC1C=CC(I)=CC=1C(Cl)=O.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[O:6]Participants
4
Procedure
2-Bromo-5-iodobenzoic acid was converted to 2-bromo-5-iodobenzoyl chloride following procedures similar to those in Example 82A. The 2-bromo-5-iodobenzoyl chloride was reacted with triethyl phosphite following procedures similar to those in Example 82 to give diethyl (2-bromo-5-iodophenyl)oxomethylphosphonate. The diethyl (2-bromo-5-iodophenyl)oxomethylphosphonate was converted to diethyl(2-bromo-5-iodophenyl)difluoromethylphosphonate following procedures similar to those in Example 80C. Compound 94 was synthesized according to procedures similar to those of Example 40 from this corresponding diethyl phosphonate. MS (ES-): m/z 411.0, 413.0 (M−H). 1H NMR: (DMSO-d6, 400 MHz) δ 7.93 (s, 1H), 7.67-7.69 (m, 1H), 7.45 (d, J=8.2, 1H).
Sources & evidence
- ORD record
- ord-d79908969d25494b9bc412519485110e
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504389B2
Reaction notes
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