C(OP([O-])OCC)C.C(N(CC)CC)C.[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([NH:35][C:36](=[O:38])[CH3:37])[CH:27]=[CH:28][C:29]=1[C:30](=[O:34])[CH:31](Br)[Br:32])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCOC(C)=O>C1COCC1>[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([NH:35][C:36](=[O:38])[CH3:37])[CH:27]=[CH:28][C:29]=1[C:30](=[O:34])[CH2:31][Br:32])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1A solution of diethylphosphite (12.6 μL, 13.5 mg, 97.6 μmol) and triethylamine (13.6 μL, 9.9 mg, 97.6 μmol) in THF (0.1 mL) was added to a stirred solution of N-[3-benzyloxy-4-(2,2-dibromo-acetyl)-phenyl]-acetamide (41 mg, 92.9 μmol) in THF (1.5 mL) at room temperature, and the reaction stirred for 2 hours. The mixture was poured into EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give N-[3-benzyloxy-4-(2-bromo-acetyl)-phenyl]-acetamide (40 mg, >100%), which was seen by NMR to be contaminated with a diethylphosphite-derived contaminant. The material could be used successfully in the following steps without further purification. All analytical data was as reported above.
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