Triethylamine → [3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl methanesulfonate

HRID 747182Notes

Reaction equation

HRID 747182 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][O:14][S:23]([CH3:22])(=[O:25])=[O:24])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15888252[3-(4-Bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol

Product 1

HCID 18698757[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl methanesulfonateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[3-(4-Bromo-phenyl)-4,5-dihydro-isoxazol-5-yl]-methanol (84.3 g, 328 mmol) was added to anhydrous dichloromethane (500 ml) followed by addition of triethylamine (64.1 ml, 459.2 mmol). The solution was allowed to cool to 0° C. followed by dropwise addition of methane sulfonyl chloride (30.65 ml, 396 mmol). The reaction was stirred for 2 hours at 0° C. and then aqueous sodium bicarbonate (200 ml) was added. After further extraction with dichloromethane (2×200 ml), the organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (110 g).

Workup

  1. extractionAfter further extraction with dichloromethane (2×200 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5de72995025d4967b05cf58a32c86df7
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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