Triethylamine → (2E)-3-(4-Fluoro-2-methoxyphenyl)-2-propenoyl azide

HRID 1852113Notes

Reaction equation

HRID 1852113 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](O)=[O:11])=[C:4]([O:13][CH3:14])[CH:3]=1.C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.CCN(CC)CC>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:29]=[N+:30]=[N-:31])=[O:11])=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23150778(2E)-3-(4-Fluoro-2-methoxyphenyl)-2-propenoic acid

Product 1

HCID 86683195(2E)-3-(4-Fluoro-2-methoxyphenyl)-2-propenoyl azideYield 76.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(E)-3-(4-fluoro-2-methoxyphenyl)acrylic acid (1.22 g, 6.22 mmol), diphenylphosphinyl azide (1.273 mL, 5.91 mmol), and Et3N (1.734 mL, 12.44 mmol) were dissolved in benzene and stirred for 16 h. The solution was concentrated under vacuum and the residue was purified by silica gel chromatography using 20% EtOAc/Hexanes to give (E)-3-(4-fluoro-2-methoxyphenyl)acryloyl azide (1.0 g, 73% yield).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d2d1140c6ef54b398004eff84696f3c1
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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