Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → Tert-butyl{4-chloro-2-[(1,1-dioxido-2,3-dihydro-1-benzothien-6-yl)ethynyl]phenoxy}acetate
Reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].I[C:20]1[CH:30]=[CH:29][C:23]2[CH2:24][CH2:25][S:26](=[O:28])(=[O:27])[C:22]=2[CH:21]=1>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:20]1[CH:30]=[CH:29][C:23]2[CH2:24][CH2:25][S:26](=[O:28])(=[O:27])[C:22]=2[CH:21]=1)([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
Following the general method as outlined in Intermediate 20, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 6-iodo-2,3-dihydro-1-benzothiophene 1,1-dioxide (Intermediate 234), the title compound was obtained as a beige solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.
Sources & evidence
- ORD record
- ord-0e037bbfada34758b12703ca36a84d9a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273769B2
Reaction notes
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