Dichloromethane → Furo[3,2-c]pyridine,2-(bromomethyl)-,hydrochloride
Reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH2:10]O.C(Br)(Br)(Br)[Br:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)[Cl:37]>>[ClH:37].[Br:13][CH2:10][C:2]1[O:1][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A stirred suspension of furo[3,2-c]pyridin-2-ylmethanol (Preparation 4, 1.47 g, 9.9 mmol) in anhydrous CH2Cl2 (60 mL) was treated with CBr4 (4.90 g, 14.8 mmol). The mixture was cooled down to 0° C., before being treated with PPh3 (3.88 g, 14.8 mmol). After 2 h at 20° C., the reaction was filtered, then the filtrate was diluted with CH2Cl2 (50 mL), before being washed with saturated aqueous NaHCO3 (2×50 mL) and H2O (50 mL). The CH2Cl2 solution was extracted with 2 M HCl (3×50 mL), then the combined HCl extracts were evaporated to furnish the title compound: m/z (ES+)=211.9, 213.9 [M+H]+.
Workup
- filtrationthe reaction was filtered
- additionthe filtrate was diluted with CH2Cl2 (50 mL)
- washbefore being washed with saturated aqueous NaHCO3 (2×50 mL) and H2O (50 mL)
- extractionThe CH2Cl2 solution was extracted with 2 M HCl (3×50 mL)
- customthe combined HCl extracts were evaporated
Sources & evidence
- ORD record
- ord-19b7c3b4703d457b93af49eebe1eef1d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193359B2
Reaction notes
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