Triethylamine → 2-Bromo-5-nitrobenzyl methanesulfonate

HRID 17038Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][OH:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][S:14]([O:12][CH2:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:16])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the (2-bromo-5-nitrophenyl)methanol from Step A (0.33 g, 1.42 mmol) in methylene chloride (20 ml) at 0° C., methanesulfonyl chloride (0.13 ml, 1.70 mmol) and triethylamine (0.3 ml, 2.1 mmol) were added. The solution was stirred at 0° C. for 1 h. The reaction was diluted with methylene chloride (30 ml). The solution was washed with water, brine, and dried over sodium sulfate. The title compound was obtained by flash column chromatography using 10:90 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 8.40 (d, J=2.5 Hz, 1H), 8.17 (dd, J=8.5, 3.0 Hz, 1H), 7.82 (d, J=8.5 Hz, 1H), 5.40 (s, 2H), 3.20 (s, 3H).

Workup

washThe solution was washed with water, brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-029f10705a414c6ab1e44d0086232a9f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737295B2

Reaction notes

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