Water → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl methanesulfonate
Reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:10]([OH:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].CCN(C(C)C)C(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C(Cl)Cl>[CH3:24][S:25]([O:12][CH:10]([C:4]1[CH:5]=[C:6]([Cl:9])[C:7]([F:8])=[C:2]([Br:1])[C:3]=1[O:13][CH3:14])[CH3:11])(=[O:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanol (3.9 g, 14 mmol) in methylene chloride (42 mL), cooled at 0° C. was added DIPEA (4.0 mL, 23 mmol) followed by methanesulfonyl chloride (1.6 mL, 20 mmol). The mixture was stirred for 1 h at 0° C. Water (100 mL) was added while cold. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated to give 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl methanesulfonate. The mesylate was dissolved in DMF (41 mL) and sodium azide (1.8 g, 27 mmol) was added. The reaction was stirred for 2 hours. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. Purification on silica gel using 0-30% EtOAc in hexane gave the desired compound (3.3 g, 78%). LCMS calculated for C9H8BrClFO (M−N3)+: m/z=264.9, 266.9. found: 265.0, 267.0.
Workup
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-543d6e84e68c42afaaeabb035e41baae
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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