N-Iodosuccinimide → (E)-ethyl 3-(4-iodophenyl)acrylate

HRID 1057183Notes

Reaction equation

HRID 1057183 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)[CH3:10]>CC#N.CCOC(C)=O>[I:1][C:18]1[CH:19]=[CH:20][C:15](/[CH:14]=[CH:13]/[C:12]([O:11][CH2:9][CH3:10])=[O:24])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 59425074-(E-3-Ethoxy-3-oxo-1-propen-1-yl)benzeneboronic acid

Product 1

HCID 21107276(E)-ethyl 3-(4-iodophenyl)acrylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Iodosuccinimide (2.5 g, 11 mmol) was added to a suspension of 4-(E-3-ethoxy-3-oxo-1-propen-1-yl)phenylboronic acid (2.2 g, 10 mmol) in CH3CN (50 mL) at room temperature. The reaction was covered with foil, stirred for 26 h, and then diluted with EtOAc. The resulting mixture was washed with water (2×100 mL), washed with sodium thiosulfate (100 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give 2.6 g of (E)-ethyl 3-(4-iodophenyl)acrylate as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, 2H), 7.60 (d, 1H), 7.53 (d, 2H), 6.68 (d, 1H), 4.19 (q, 2H), 1.26 (t, 3H); LCMS: 303 (M+H)+.

Workup

  1. washThe resulting mixture was washed with water (2×100 mL)
  2. washwashed with sodium thiosulfate (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-80fed62a93c8441ca1baaa323d5d139b
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

Loading…