Acetic Acid → HCID 58669189, compound

HRID 1444996Notes

Reaction equation

HRID 1444996 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:7]=1[CH3:8])=[O:2].C(O)(=O)C.C(Cl)(Cl)Cl.[Br:23]N1C(=O)CCC1=O>O>[Br:23][C:5]1[S:4][C:3]([CH:1]=[O:2])=[C:7]([CH3:8])[C:6]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 58669199HCID 58669199, compound

Product 1

HCID 58669189HCID 58669189, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-formyl-3-methyl-4-cyclohexylthiophene (4.1 g, 20 mmol, See Example 22) in 30 mL of a mixture prepared from acetic acid and chloroform (1:1), was added solid N-bromosuccinimide (5.3 g, 30 mmol) slowly in portions at 0° C. The reaction mixture was then stirred overnight at room temperature, poured into water, and extracted repeatedly with dichloromethane. The combined organic layers were washed with saturated NaHCO3 and brine solutions, and dried over anhydrous Na2SO4. After the solvent was removed by rotary evaporation, the remaining solid was purified by column chromatography using silica gel and a dichloromethane-petroleum ether (2:3) as eluant. The solvent was removed by rotary evaporation yielding 3.3 g white solid (57%). 1H NMR (CDCl3) δ 9.97 (s, 1, CHO), 2.88 (m, 1,cyclohexyl methane), 2.59 (s, 3,CH3), 1.87 and 1.34 m, 10, cyclohexyl)

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. washThe combined organic layers were washed with saturated NaHCO3 and brine solutions
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter the solvent was removed by rotary evaporation
  5. customthe remaining solid was purified by column chromatography
  6. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-7b56100f55064b32a9527f27356dc14e
Source dataset
uspto-grants-2010_02
Patent number
US07663301B2

Reaction notes

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