1-Bromo-4-hexylbenzene → 2-(4-Hexylphenyl)-6-octyloxybenzo[b]thiophene
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9](B(O)O)[S:8][C:7]=2[CH:14]=1.[CH2:15]([C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:15]([C:21]1[CH:26]=[CH:25][C:24]([C:9]2[S:8][C:7]3[CH:14]=[C:3]([O:2][CH2:1][CH2:5][CH2:4][CH2:3][CH2:14][CH2:7][CH2:6][CH3:10])[CH:4]=[CH:5][C:6]=3[CH:10]=2)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]Participants
3
Procedure
is prepared analogously to Reference 14 (p. 16) from 6-methoxybenzo[b]thiophene-2-boronic acid and 4-hexylbromobenzene in a Suzuki reaction. The 2-(4-hexylphenyl)-6-methoxybenzo[b]thiophene obtained as the primary product is subjected to ether cleavage by means of hydrobromic acid/glacial acetic acid. The resultant hydroxyl compound gives the target compound in a Williamson ether synthesis using octyl bromide in 2-butanone in the presence of potassium carbonate.
Sources & evidence
- ORD record
- ord-5846fb77c21742d2804e9dc5c6c7b83e
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403172B1
Reaction notes
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