Triphenylphosphine → 2-Acetoxy-5-(4-benzoyl-2,6-diiodo-phenoxymethyl)-benzoic acid methyl ester

HRID 1107931Notes

Reaction equation

HRID 1107931 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](CO)=[CH:6][C:5]=1[O:12][C:13](=[O:15])[CH3:14].[OH:17][C:18]1[C:23]([I:24])=[CH:22][C:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])=[CH:20][C:19]=1[I:33].[C:34]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH2:34][O:17][C:18]2[C:19]([I:33])=[CH:20][C:21]([C:25](=[O:26])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][C:23]=2[I:24])[CH:7]=[CH:6][C:5]=1[O:12][C:13](=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9911585(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanoneHCID 54078316HCID 54078316, compound

Product 1

HCID 98744162-Acetoxy-5-(4-benzoyl-2,6-diiodo-phenoxymethyl)-benzoic acid methyl esterYield 54.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared according to the procedure in Example 1, step 5 using 2-acetoxy-4-(hydroxymethyl) benzoic acid methyl ester (0.109 g, 0.484 mmol), (4-hydroxy-3,5-diiodo-phenyl)-phenyl-methanone (0.218 g, 0.484 mmol), triphenylphosphine (0.140 g, 0.533 mmol) and diethylazodicarboxylate (83.5 μL, 0.533 mmol) in benzene (4.84 mL). Purification on Biotage KP-Sil eluting with a 10, 15 & 20% EtOAc/pet. ether gave 0.173 g (54%) of the title compound as a white solid, mp 132-135° C. 1H NMR (DMSO-d6) δ 2.30 (s, 3H), 3.83 (s, 3H), 5.09 (s, 2H), 7.35 (d, 1H), 7.58 (t, 2H), 7.69-7.75 (m, 3H), 7.92 (dd, 1H), 8.13 (d, 2H), 8.19 (d, 1 H). IR (KBr) 2950, 1760, 1220, 1660 and 1275 cm-1. mass spectrum (+FAB) m/z 657 (M+H), 679 (M+Na).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 10, 15 & 20% EtOAc/pet. ether

Sources & evidence

ORD record
ord-7d5c9fb348eb4b27a179940120f90627
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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