Methanesulfonyl chloride → 3-(1-Chloroethyl)-4-phenyl-1H-isochromen-1-one

HRID 634399Notes

Reaction equation

HRID 634399 reaction equation
O[CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].CS([Cl:25])(=O)=O>C(Cl)Cl>[Cl:25][CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1181311643-(1-Hydroxyethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 1181314543-(1-Chloroethyl)-4-phenyl-1H-isochromen-1-oneYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-Hydroxyethyl)-4-phenyl-1H-isochromen-1-one (intermediate B1, 300 mg, 1.27 mmol), Methane sulfonyl chloride (516 mg, 4.51 mmol), TEA (0.62 mmol, 4.5 ml) were reacted in DCM (10 ml) at RT. Solvent was then removed under reduced pressure to give the title compound (180 mg). This was used in next step without any further purification.

Workup

  1. customSolvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-b8b32a77efcd43ea8edd0c08b5a87a12
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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