Acetic Acid → HCID 178501035, compound

HRID 1508524Notes

Reaction equation

HRID 1508524 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C1C(=O)N([I:30])C(=O)C1.C(O)(=O)C>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]2)=[CH:11][C:12]=1[I:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 178501034HCID 178501034, compound

Product 1

HCID 178501035HCID 178501035, compound

Procedure

Sulfuric acid (0.708 mL, 13.29 mmol) was added into a cold (ice bath) mixture of methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate (3.3588 g, 13.29 mmol) and n-iodosuccinimide (2.99 g, 13.29 mmol) in acetic acid (0.798 g, 13.29 mmol). The reaction mixture was stirred in an ice bath and was allowed to warm to ambient temperature overnight. The reaction crude was poured into an ice water and extracted with EtOAc. The separated organic phase was dried over Na2SO4, filtered and evaporated to afford a dark mixture. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by a EtOAc/hexanes mixture (0% to 10%). Related fractions were pooled and evaporated to afford a crystalline solid as the titled compound. LCMS calc.=377.99. found=379.00 (M+H)+.

Workup

  1. customThe reaction crude
  2. extractionextracted with EtOAc
  3. dry with materialThe separated organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a dark mixture
  7. customThe resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge)
  8. washThe column was eluted by a EtOAc/hexanes mixture (0% to 10%)
  9. customevaporated

Sources & evidence

ORD record
ord-6ada57bdd8bf421f805a9029a7bd2554
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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