4-Iodobenzoic acid → 158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

HRID 1884206

Reaktionsgleichung

Reaktionsgleichung von HRID 1884206
B(OC(C)C)(OC(C)C)OC(C)C.I[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.[CH2:24]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)[CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:24]([O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][C:39]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[CH:38][CH:37]=2)=[CH:34][CH:35]=1)[CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

4

Edukt 3

HCID 120854-Iodobenzoic acidHCID 21531Triisopropyl borateHCID 113580714'-Pentyloxybiphenyl-4-boronic Acid

Produkt 1

HCID 9798987158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

Versuchsvorschrift

In a first step, 4′-bromo-4-hydroxybiphenyl is reacted with an n-pentyl halide to give the corresponding 4′-bromo-4-n-pentoxybiphenyl. The 4′-bromo-4-n-pentoxybiphenyl is reacted in a second step with n-butyllithium at −78° C. to form, by transmetallation, 4′-lithium-4-n-pentoxybiphenyl which, in another step likewise at −78° C., is reacted with triisopropyl borate. Hydrolysis and work-up result in 4′-n-pentoxybiphenyl-4-boronic acid which is reacted in further steps with 4-iodobenzoic acid in a standard Suzuki coupling. The 4″-n-pentoxy[1,1′:4′,1″]-terphenyl-4-carboxylic acid is obtained as crude product which is purified by chromatography on silica gel.

Aufarbeitung

  1. customHydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-48beeecbfadc4539802f36ccdcca8b83
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762315B1

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