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

HRID 2425279Notes

Reaction equation

HRID 2425279 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, l=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-efaadd103a804e22b2752b045e0defc9
Source dataset
uspto-grants-2011_06
Patent number
US07964650B2

Reaction notes

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