Triethylamine → (E)-1-Chloro-4-(2-tosylvinyl)benzene

HRID 623722Notes

Reaction equation

HRID 623722 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](I)[CH2:9][S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:4][CH:3]=1.CCN(CC)CC>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:17])=[CH:18][CH:19]=2)(=[O:11])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86711813HCID 86711813, compound

Product 1

HCID 10979228(E)-1-Chloro-4-(2-tosylvinyl)benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Chloro-4-(1-iodo-2-tosylethyl)benzene (28.5 g, 67.7 mmol) was dissolved in dry MeCN (376 mL) followed by addition of Et3N (18.83 mL, 135 mmol) and the mixture was stirred at room temperature for 1 h. Then the solvent was evaporated under reduced pressure and the residue partitioned between DCM (400 mL) and 1M aqueous KHSO4 (300 mL). The layers were separated and the organic phase was dried over Na2SO4, filtered and evaporated to dryness under reduced pressure to afford 19 g (96%) of the desired product.

Workup

  1. customThen the solvent was evaporated under reduced pressure
  2. customthe residue partitioned between DCM (400 mL) and 1M aqueous KHSO4 (300 mL)
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-54e42c48060c417fb8cb1a0a23734422
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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