Triethylamine → HCID 59749462, compound

HRID 747187Notes

Reaction equation

HRID 747187 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][C:3]=1[F:15].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][O:14][S:24]([CH3:23])(=[O:26])=[O:25])[O:10][N:9]=2)=[CH:4][C:3]=1[F:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 17954502HCID 17954502, compound

Product 1

HCID 59749462HCID 59749462, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[3-(4-Bromo-3-fluoro-phenyl)-4,5-dihydro-isoxazol-5-yl]-methanol (30 g, 112.4 mmol) was added to anhydrous dichloromethane (300 ml) followed by addition of triethylamine (21.8 ml, 157.3 mmol). The solution was cooled to 0° C. followed by drop wise addition of methane sulfonyl chloride (10.4 ml, 134.8 mmol). The reaction was stirred for 2 hours at 0° C. and then aqueous sodium bicarbonate (100 ml) was added. After further extraction with dichloromethane (2×100 ml), the organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (38.7 g).

Workup

  1. extractionAfter further extraction with dichloromethane (2×100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-807eed1964034e9295d6d2d594c9f68f
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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