Triethylamine → (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester

HRID 602273Notes

Reaction equation

HRID 602273 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][C:3]=1[O:10][CH3:11].[CH3:12][O:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][O:19][C:20](=[O:38])[C:21]2[CH:26]=[C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[CH:24]=[CH:23][C:22]=2I)=[CH:16][CH:15]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:20](=[O:38])[C:21]2[CH:26]=[C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[CH:24]=[CH:23][C:22]=2/[CH:9]=[CH:8]/[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:10][CH3:11])[CH:4]=2)=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 230701471-Fluoro-2-methoxy-4-vinylbenzeneHCID 596842532-Iodo-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester

Product 1

HCID 59684249(E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-fluoro-2-methoxy-4-vinylbenzene (INTERMEDIATE I.1) (4.49 g, 29.53 mmol) and 2-iodo-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester (14.89 g, 29.53 mmol) in anhydrous acetonitrile (75 mL) was added triethylamine (8.2 mL, 59.06 mmol) and tri(o-tolyl)phosphine (1.17 g, 3.84 mmol). The mixture was sparged for 5 min with argon, and palladium(II) acetate (662 mg, 2.95 mmol) was added. The mixture was heated at reflux for 13 h and concentrated to give the crude product (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester as a dark brown residue, which was used without further purification.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 13 h
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-393cb825eb384ee69f1c83898c7602c9
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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