Triethylamine → 2,2-Bis(3-bromophenyl)propane-1,3-diyl dimethanesulfonate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)([CH2:11][OH:12])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CCN(CC)CC>ClCCl>[CH3:20][S:21]([O:12][CH2:11][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1)([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:9][O:10][S:21]([CH3:20])(=[O:23])=[O:22])(=[O:23])=[O:22]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 2,2-bis(3-bromophenyl)propane-1,3-diol (6.0 g, 15.54 mmol) in dichloromethane (50 mL) at 0° C. was added methanesulfonic chloride (27.1 g, 155 mmol) and Et3N (17.3 mL, 124 mmol) to give an orange solution. The reaction mixture was stirred at 0° C. for 1 h, then at 40° C. for 8 h. The reaction was washed with aq. NH4Cl (80 mL). The aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layers were dried and concentrated. The residue was purified by chromatography (on silica gel column, Petroleum ether: EtOAc=2:1) to afford 3.2 g of the title compound (5.9 mmol, 38%). LC/MS: [M+18]=560. 1HNMR (CDCl3), 400 MHz: δ 2.93 (s, 6H), 4.49 (s, 4H), 7.15-7.48 (m, 8H).
Workup
- customto give an orange solution
- waitat 40° C. for 8 h
- washThe reaction was washed with aq. NH4Cl (80 mL)
- extractionThe aqueous layer was extracted with dichloromethane (50 mL×3)
- customThe combined organic layers were dried
- concentrationconcentrated
- customThe residue was purified by chromatography (on silica gel column, Petroleum ether: EtOAc=2:1)
Sources & evidence
- ORD record
- ord-5ff7831406fc4eb9b2377cd0b55d4bae
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937150B2
Reaction notes
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