p-Toluenesulfonic acid → Ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate
Reaction equation
[C:1]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1C(=O)N([Br:19])C(=O)C1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Br:19][CH2:2][C:1]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1)=[O:3]Participants
4
Procedure
To a 100 mL of round-bottomed flask was added ethyl 1-acetylcyclopropanecarboxylate (15.6 g, 100 mmol) and NBS solid (21.36 g, 120 mmol), followed by p-toluene sulfonic acid (1.9 g, 10 mmol). After stirring at rt for 8 hrs, the reaction mixture was extracted with diethyl ether (200 mL) and washed with 80 mL of water. The organic phase was then dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:30(v/v) EtOAc/n-hexane) to give the title compound as colorless oil (16.68 g, 71%).
Workup
- extractionthe reaction mixture was extracted with diethyl ether (200 mL)
- washwashed with 80 mL of water
- dry with materialThe organic phase was then dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (1:30(v/v) EtOAc/n-hexane)
Sources & evidence
- ORD record
- ord-fa3bd5fa459d4f45a841d87f28729180
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426585B2
Reaction notes
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