Imidazole → Methyl 5-(bromomethyl)thiophene-2-carboxylate
Reaction equation
[Br:1]Br.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:28][C:29]1[S:33][C:32]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:30]=1>C(Cl)Cl>[Br:1][CH2:28][C:29]1[S:33][C:32]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:30]=1Participants
6
Procedure
Bromine (0.47 mL, 9.12 mmol) was added to a solution of imidazole (617 mg, 9.06 mmol) and triphenylphosphine (2.40 g, 9.15 mmol) in CH2Cl2 (30 mL) at room temperature. A solution of methyl 5-hydroxymethyl-thiophene-2-carboxylate (prepared according to the procedures described in WO2004/037808; 1.30 g, 7.59 mmol) in CH2Cl2 (10 mL) was then added. After 10 min at room temperature, the reaction mixture was concentrated in vacuo. Purification of the crude residue by flash column chromatography on 80 g of silica gel (hexane→EtOAc, gradient) afforded 1.70 g (95%) of the title compound (B).
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- customPurification of the crude residue by flash column chromatography on 80 g of silica gel (hexane→EtOAc, gradient)
Sources & evidence
- ORD record
- ord-64b3ab64a82f4dccbb405c64e6a12340
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786154B2
Reaction notes
Loading…