Bromine → (4-Bromothiophen-2-yl)(cyclopropyl)methanone

HRID 656107Notes

Reaction equation

HRID 656107 reaction equation
[CH:1]1([C:4]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:9]1[CH:10]=[C:6]([C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[S:7][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 80328Cyclopropyl-2-thienylmethanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59332599(4-Bromothiophen-2-yl)(cyclopropyl)methanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Cyclopropyl(2-thienyl)methanone (Aldrich, 1.5 g, 9.9 mmol) was diluted in chloroform (10 mL). Aluminum chloride (2.96 g, 22.2 mmol, 2.3 eq) was added, followed by the dropwise addition of bromine (0.56 mL, 11 mmol, 1.1 eq) in chloroform (10 mL). The mixture was stirred at rt overnight, then poured onto ice water (100 mL). The whole was extracted with dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated to give brown oil. The crude product was purified by isco combiflash, 120 g column, eluting with 0-15% ethyl acetate in hexanes. Yellow oil was obtained.

Workup

  1. additionpoured onto ice water (100 mL)
  2. extractionThe whole was extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give brown oil
  7. customThe crude product was purified by isco combiflash, 120 g column
  8. washeluting with 0-15% ethyl acetate in hexanes
  9. customYellow oil was obtained

Sources & evidence

ORD record
ord-83c896806e754338bf7fbc1857a04d6a
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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