t-Butyl bromide → 5-(1,1-Dimethylethyl)-3-thiophenecarboxaldehyde

HRID 235087Notes

Reaction equation

HRID 235087 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH3:8][C:9](Br)([CH3:11])[CH3:10]>C(Cl)Cl>[CH3:8][C:9]([C:5]1[S:1][CH:2]=[C:3]([CH:6]=[O:7])[CH:4]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 10485t-Butyl bromideHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 233535855-(1,1-Dimethylethyl)-3-thiophenecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.63 g (32.4 mmol) of 3-thiophenecarboxaldehyde (Aldrich Chemical Co.) in 60 mL of methylene chloride cooled to 0° C. was added 9.17 g (80.9 mmol) of AICl3 and 2-methyl-2-bromopropane. The solution was stirred under N2 at room temperature for 16 hours and at reflux for 4 hours. The solution was then cooled to room temperature, and the reaction was quenched by pouring the solution into water. The mixture was made basic with aqueous NaHCO3 and extracted with ether. The ether extract was washed with water, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel, eluting with 15:1 hexane:ethyl acetate, to afford 2.23 g of the title product as an oil, after removal of the solvent. NMR (CD3OD) δ:1.41 (s, 9H), 7.26 (d, 1 H, J=1 Hz), 8.2 (d, 1H, J=l Hz), 9.78 (s, 1H).

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe solution was then cooled to room temperature
  3. customthe reaction was quenched
  4. additionby pouring the solution into water
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel
  11. washeluting with 15:1 hexane

Sources & evidence

ORD record
ord-2fd8bdb39f774183abf2732b63b3b6d5
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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