Dichloromethane → HCID 69275389, compound

HRID 2375382Notes

Reaction equation

HRID 2375382 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2].B(Br)(Br)Br.C(Cl)Cl>>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 393723951-[1-(2,4-Dimethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Product 1

HCID 69275389HCID 69275389, compound

Procedure

To a solution of 3-acetyl-1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (2.73 g, 10 mmol) (EXAMPLE 33) in CH2Cl2at rt (75 mL) was added a 1.0M solution of boron tribromide in CH2Cl2 (15 mL, 15 mmol) and the reaction monitored by LC. After complete consumption of the starting material, the reaction was carefully quenched with saturated NaHCO3 and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography to give 3-acetyl-2,5-dimethyl-1-(4-hydroxy-2-methoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 6.92 (d, 1H), 6.61 (d, 1H), 6.54 (dd, 1H), 6.32 (s, 1H), 3.72 (s, 3H), 2.44 (s, 3H), 2.26 (s, 3H), 1.93 (s, 3H), 1.69 (br s, 1H); MS (ESI) 260 (M+H)+.

Workup

  1. customAfter complete consumption of the starting material
  2. customthe reaction was carefully quenched with saturated NaHCO3
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ee4b61021eb24c619151a261c472286c
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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