Pyridine → 2-(3-Bromopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:12][CH:11]([CH2:13][CH2:14][CH2:15]O)[S:10][C:9]=2[C:17]=1[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.[Br:46]Br>C1C=CC=CC=1.O>[Br:46][CH2:15][CH2:14][CH2:13][CH:11]1[S:10][C:9]2[C:17]([CH3:18])=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]=2[O:12]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2.6 g of 3-(5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 85) and 4.6 g of triphenylphosphine were dissolved in 30 ml of benzene, and 3 ml of dry pyridine were added to the solution. 4.4 g of bromine were then added dropwise at room temperature to this reaction mixture. The temperature rose as the bromine was added, and the mixture was allowed to stand until this temperature rise had finished and the mixture had returned to room temperature. The reaction mixture was then stirred for 40 minutes at room temperature, whereupon crystals formed. Water was added to the reaction mixture, which was then extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The benzene was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography. The title compound was obtained from the fraction eluted with a 2:3 by volume mixture of cyclohexane and benzene.
Workup
- additionwas added
- customhad returned to room temperature
- customformed
- extractionwas then extracted with benzene
- washThe extract was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe benzene was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-b481e08d0ae346249966e1462006aa91
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04871762
Reaction notes
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