Carbon tetrabromide → tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([O:29][C:30](=[O:40])[NH:31][C:32]1[CH:37]=[CH:36][C:35](CO)=[CH:34][N:33]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30](=[O:40])[NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:20][Br:24])=[CH:34][N:33]=1)([CH3:28])([CH3:26])[CH3:27]Participants
5
Conditions
- Temperature
- -20 °C
Procedure
Triphenylphosphine (8.70 g, 33.1 mmol) and carbontetrabromide (17.0 g, 51.2 mmol) were added to a suspension of (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g 31.2 mmol) in CH2Cl2 (200 mL) at room temperature. Stirring was continued for 5 h followed by evaporation of the solvent. Acetonitrile (200 mL) was added and the mixture was cooled to −20° C. for 2 h. The mixture was then filtered and the crystalline residue washed with cold acetonitrile (2×10 mL), to give (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (5.96 g, 67%).
Workup
- customfollowed by evaporation of the solvent
- additionAcetonitrile (200 mL) was added
- filtrationThe mixture was then filtered
- washthe crystalline residue washed with cold acetonitrile (2×10 mL)
Sources & evidence
- ORD record
- ord-40c9ef8798c5405c862f433fe954dac4
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071175B1
Reaction notes
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