Ethyl Acetate → 4-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidine

HRID 575631Notes

Reaction equation

HRID 575631 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][N:5]=[C:4](SC)[N:3]=1.[CH:19]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:30][S:31]([O-:33])=O.[Na+].[Na+].CC(=O)OCC>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][N:5]=[C:4]([S:31]([CH3:19])(=[O:33])=[O:30])[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 1180215104-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfanylpyrimidine

Product 1

HCID 1180215444-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidineYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of the title compound of step 2 (4.60 g, 15.93 mmol) in CH2Cl2 (200 mL) was added mCPBA (13.75 g, 79.68 mmol) slowly at 0° C. The mixture was stirred at 20° C. for 12 h and then sat. aq. Na2SO3 (200 mL) was added. EA extractive work up and silica gel chromatography gave the title compound (2.0 g, 39.1% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.18 (s, 1H), 7.31-7.27 (m, 1H), 7.10-7.01 (m, 2H), 3.36 (s, 3H). LCMS: 320.8 (M+1)+

Sources & evidence

ORD record
ord-e97dd5c1ca2e40309fe7d494e9d1ffb3
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…