Ethanol → HCID 89739679, compound

HRID 1521804Notes

Reaction equation

HRID 1521804 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[C:8]1[S:9][C:10]([C:12](=[O:14])[CH3:13])=[CH:11][C:7]=1[CH:6]=[CH:5]2.OC1C([O:26][S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])=C(I)C=CC=1.C(O)C>C(#N)C>[CH3:34][C:33]1[CH:32]=[CH:31][C:30]([S:27]([O:29][CH2:13][C:12]([C:10]2[S:9][C:8]3[C:15]4[C:4]([CH:5]=[CH:6][C:7]=3[CH:11]=2)=[CH:3][C:2]([Br:1])=[CH:17][CH:16]=4)=[O:14])(=[O:28])=[O:26])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 21918218Hydroxy tosyloxy iodobenzeneHCID 89740004HCID 89740004, compound

Product 1

HCID 89739679HCID 89739679, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(7-bromonaphtho[1,2-b]thiophen-2-yl)ethanone (11c) (1.26 g, 4.13 mmol) in 15 ml of acetonitrile at 75° C., hydroxytosyloxyiodobenzene (2.59 g, 6.61 mmol) was added and the mixture was refluxed for 8 hr. The volume of acetonitrile was reduced under vacuum and ethanol was added to it. The orange solid obtained was filtered and washed with ether to obtain the desired compound (11d) (1.6 g, 82%).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. additionwas added to it
  3. customThe orange solid obtained
  4. filtrationwas filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-490ceeadca69435fbc700064d6f89324
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

Loading…