2-Bromothiophene → 1-(5-Bromothiophen-2-YL)heptan-1-one

HRID 490855Notes

Reaction equation

HRID 490855 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7](Cl)(=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[C:7]([C:4]1[S:3][C:2]([Br:1])=[CH:6][CH:5]=1)(=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 138512-BromothiopheneHCID 17313Heptanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 576755661-(5-Bromothiophen-2-YL)heptan-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Bromothiophene (1.63 g, 10.0 mmol) and heptanoyl chloride (1.78 g, 12.0 mmol) were dissolved in dry benzene (15 mL) and AlCl3 was added in portions with stirring over 10 min. The resulting dark brown solution was refluxed for 1 hr and left to cool down to room temperature. The mixture was quenched with 2M HCl (15 mL) carefully while stirred. The organic layer was separated, washed with 2M HCl, 2M NaOH, and water, and passed through silica column (d=3 cm, I=8 cm). The solution was dried over MgSO4, and concentrated in vacuo (2.40 g, 87%).

Workup

  1. temperatureThe resulting dark brown solution was refluxed for 1 hr
  2. waitleft
  3. customThe mixture was quenched with 2M HCl (15 mL) carefully
  4. stirringwhile stirred
  5. customThe organic layer was separated
  6. washwashed with 2M HCl, 2M NaOH, and water
  7. dry with materialThe solution was dried over MgSO4
  8. concentrationconcentrated in vacuo (2.40 g, 87%)

Sources & evidence

ORD record
ord-f2505e8950b24c6d8d33be1cc40a5d5b
Source dataset
uspto-grants-2009_05
Patent number
US07528176B2

Reaction notes

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