Chlorosuccinimide → 6-Chloro-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 2202441

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C1C(=O)N([Cl:23])C(=O)C1>CC#N>[Cl:23][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[C:10]([CH3:13])([CH3:14])[C:9](=[O:15])[CH2:8][CH2:7]2

Participants

Conditions

Temperature: 90 °C

Procedure

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 3.37 g, 16.5 mmol) was dissolved in CH3CN (82 mL), added with NCS (2.42 g, 1.1 eq.) and stirred at 90° C. for 1.5 hours. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed and the target compound was obtained after concentration under reduced pressure (yellow oily substance, 4.45 g).

Workup

extractionThe reaction solution was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customThe drying agent was removed
customthe target compound was obtained
concentrationafter concentration under reduced pressure (yellow oily substance, 4.45 g)

Sources & evidence

ORD record: ord-0b38050f66044216b64db0c41abe25ec
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365514B2

Linked notes

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