4-Bromophenol → 2-[2-(4-Benzyloxyphenylethynyl)-4-methoxyphenyl]-6-methoxy-1,2,3,4-tetrahydronaphthalene

HRID 2423875

Reaction equation

BrC1C=CC(O)=CC=1.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[CH:34]1[CH2:43][CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH3:45])[CH:40]=2)[CH2:35]1>>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=2[CH:34]2[CH2:43][CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH3:45])[CH:40]=3)[CH2:35]2)=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 78084-Bromophenol

HCID 14903234'-Benzyloxyphenyl acetylene

HCID 230875592-(2-Iodo-4-methoxyphenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 666272732-[2-(4-Benzyloxyphenylethynyl)-4-methoxyphenyl]-6-methoxy-1,2,3,4-tetrahydronaphthaleneYield 67.3%

Procedure

Synthesized from 4-bromophenol according to an analogous synthetic method to Preparation Example 117 described below, 1-benzyloxy-4-ethynylbenzene (470 mg) and 2-(2-iodo-4-methoxyphenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene (690 mg) were used according to an analogous synthetic method to Preparation Example 45 to provide 2-[2-(4-benzyloxyphenylethynyl)-4-methoxyphenyl]-6-methoxy-1,2,3,4-tetrahydronaphthalene (559 mg). This compound (557 mg) was used according to an analogous synthetic method to Example 22 to provide the title compound (482 mg).

Workup

customwere used according to an analogous synthetic method to Preparation Example 45

Sources & evidence

ORD record: ord-3217dac4cadb46c4ac222a9d606c9a45
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960412B2

Linked notes

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