(4-Formylthiophen-3-yl)boronic acid → 4-(4-Chlorobenzyl)thiophene-3-carbaldehyde

HRID 1363258

Reaktionsgleichung

Reaktionsgleichung von HRID 1363258
P(OCC)(OCC)(O[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[CH:18]([C:20]1[C:21](B(O)O)=[CH:22][S:23][CH:24]=1)=[O:19].ClC1C=CC(CC2SC(C=O)=CC=2)=CC=1>>[Cl:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:21]2[C:20]([CH:18]=[O:19])=[CH:24][S:23][CH:22]=2)=[CH:10][CH:9]=1

Komponenten

4

Edukt 3

HCID 4190637(4-Formylthiophen-3-yl)boronic acidHCID 112774384-Chlorobenzyl diethyl phosphateHCID 201615005-(4-Chlorobenzyl)thiophene-2-carbaldehyde

Produkt 1

HCID 596486684-(4-Chlorobenzyl)thiophene-3-carbaldehydeAusbeute 58 %

Versuchsvorschrift

The title compound was synthesized from 4-chlorobenzyl diethyl phosphate and 4-formylthiophen-3-ylboronic acid using the conditions to synthesize 5-(4-chlorobenzyl)thiophene-2-carbaldehyde (Example 1.1.a). Purification by prep-TLC (50% heptane/DCM, double elution) yielded 266 mg of 4-(4-chlorobenzyl)thiophene-3-carbaldehyde (58%). 1H NMR (400 MHz, CDCl3) δ ppm 4.25 (s, 2H), 6.84-6.88 (m, 1H), 7.14-7.19 (m, 2H), 7.25-7.30 (m, 2H), 8.12 (d, J=3.17 Hz, 1H), 9.96 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 185.52, 140.84, 140.28, 140.02, 138.06, 132.10, 130.31, 128.58, 124.75, 34.70; LCMS-MS (ESI+) 236.68 (M+H).

Aufarbeitung

  1. customPurification
  2. washby prep-TLC (50% heptane/DCM, double elution)

Quellen und Nachweise

ORD-Eintrag
ord-205186a453c341358d16a94961bf5aa8
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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