Toluene → HCID 69367872, compound

HRID 1825168Notes

Reaction equation

HRID 1825168 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[I:14])=O.C1(P(=[CH:36][C:37]([O:39][CH3:40])=[O:38])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]1(C)C=CC=CC=1>>[CH2:40]([O:39][C:37](=[O:38])[CH:36]=[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[I:14])[C:2]([F:16])([F:15])[F:1])[CH3:41]

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 221434932,2,2-Trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide

Product 1

HCID 69367872HCID 69367872, compoundYield 87%

Procedure

A solution of 2,2,2-trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide 76b (4.6 g, 13.3 mmole) and methyl (triphenylphosphoranylidene)acetate (8.7 g, 25 mmole) in 50 ml toluene was brought to reflux for 5 hours and cooled to room temperature. The solution was concentrated, in vacuo and purified by column chromatography (eluting with 2–6% EtOAc in hexanes) to give 4.8 g product (87% yield). 1H NMR (300 MHz, CDCl3) δ 9.57 (1H, s), 7.68 (1H, d, J=8.8 Hz), 6.83 (1H, d, J=2.8 Hz), 6.57 (1H, dd, J=2.8, 8.8 Hz), 5.43 (1H, s), 4.23 (2H, m), 3.76 (3H, s),1.55 (3H, s), 1.31 (3H, m).

Workup

  1. temperatureto reflux for 5 hours
  2. concentrationThe solution was concentrated, in vacuo
  3. custompurified by column chromatography (eluting with 2–6% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ce4c6baa9403476ba3956bce37c9e17e
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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