Sodium Azide → 3-Azido-2,2-bis(3-bromophenyl)propyl methanesulfonate

HRID 1429272Notes

Reaction equation

[CH3:1][S:2]([O:5][CH2:6][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)[CH2:8]OS(C)(=O)=O)(=[O:4])=[O:3].CN1C(=O)N(C)CCC1.[N-:37]=[N+:38]=[N-:39].[Na+]>CCOC(C)=O>[CH3:1][S:2]([O:5][CH2:6][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)[CH2:8][N:37]=[N+:38]=[N-:39])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2,2-bis(3-bromophenyl)propane-1,3-diyl dimethanesulfonate (3.6 g, 6.64 mmol) in DMPU (25 mL, 207 mmol) under N2 was added NaN3 (0.52 g, 7.97 mmol) with stirring. The mixture was heated to 110° C. for 5 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc (100 mL), and washed with water (30 mL×2) and brine (25 mL), dried and concentrated. The residue was purified by column chromatography (on silica gel, eluent with Petroleum ether: EtOAc=3:1) to afford 1.3 g of the title compound (2.66 mmol, 40%). LC/MS: [M+18]=507. 1HNMR (CDCl3), 400 MHz: δ 2.83 (s, 3H), 4.07 (s, 2H), 4.77 (s, 2H), 7.07-7.09 (m, 2H), 7.21-7.31 (m, 4H), 7.44-7.46 (m, 2H).

Workup

temperatureAfter cooling to room temperature
washwashed with water (30 mL×2) and brine (25 mL)
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (on silica gel, eluent with Petroleum ether: EtOAc=3:1)

Sources & evidence

ORD record: ord-aa087781c5604b5b8b70023646f295da
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937150B2

Reaction notes

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