Triethylamine → HCID 86670008, compound

HRID 920526Notes

Reaction equation

HRID 920526 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.C1COCC1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:3][C:4]=1[C:11]([F:12])([F:13])[F:14])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27751081-[4-Hydroxy-2-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 86670008HCID 86670008, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-hydroxy-2-trifluoromethyl-phenyl)-ethanone (29.74 g; 145.7 mmol) in CH2Cl2 (300 mL) and THF (120 mL) was added Et3N (24.4 mL; 174.8 mmol), at 0° C. To the resulting mixture was added dropwise a solution of methanesulfonyl chloride (12.5 mL; 160.3 mmol) in CH2Cl2 (60 mL), at 0° C. Subsequently the mixture was stirred overnight at RT, and poured in ice-water. The layers were separated and the organic layer was washed with 1 M aqueous HCl and water; dried (MgSO4), filtered and concentrated in vacuo to afford methanesulfonic acid 4-acetyl-3-trifluoromethyl-phenyl ester (40.47 g), which was used as such.

Workup

  1. customat 0° C
  2. customat 0° C
  3. customThe layers were separated
  4. washthe organic layer was washed with 1 M aqueous HCl and water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c06fd158857d478ba17931958e07562d
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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