Triethylamine → 2-(4-Bromophenoxy)ethyl methanesulfonate
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.CCN(CC)CC.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(4-Bromo-phenoxy)-ethanol (125 g, 0.576 mol) was dissolved in CH2Cl2 (650 mL), and the sol. was cooled to 0° C. Et3N (110 mL, 0.864 mol), then mesyl chloride (67.1 mL, 0.864 mol) were dropped at such a speed that the temperature did not raise above 10° C. (about 60 min). The mixture was stirred at 0° C. for 1 h, then at rt overnight. The mixture was diluted with CH2Cl2, and washed with brine (2×). The aq. phase was extracted back with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (174 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min.
Workup
- temperaturedid not raise above 10° C. (about 60 min)
- customat rt
- customovernight
- washwashed with brine (2×)
- extractionThe aq. phase was extracted back with CH2Cl2
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customDrying the residue under high vacuum
Sources & evidence
- ORD record
- ord-aca6c03849284f86b3313dddff0b1eaf
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968720B2
Reaction notes
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