Iodobenzene → 4-Phenylthiophene-3-carbaldehyde

HRID 1363257

반응식

HRID 1363257 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[C:11](B(O)O)=[CH:12][S:13][CH:14]=1)=[O:9].ClC1C=CC(CC2SC(C=O)=CC=2)=CC=1>>[C:2]1([C:11]2[C:10]([CH:8]=[O:9])=[CH:14][S:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 11575IodobenzeneHCID 4190637(4-Formylthiophen-3-yl)boronic acidHCID 201615005-(4-Chlorobenzyl)thiophene-2-carbaldehyde

생성물 1

HCID 154458874-Phenylthiophene-3-carbaldehyde수율 48%

실험 절차

The title compound was synthesized from iodobenzene and 4-formylthiophen-3-ylboronic acid using the conditions to synthesize 5-(4-chlorobenzyl)thiophene-2-carbaldehyde. Double elution by prep-TLC (10% heptane/DCM) allowed for the isolation of 4-phenylthiophene-3-carbaldehyde (300 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (d, J=3.29 Hz, 1H), 7.39-7.50 (m, 5H), 8.27 (d, J=3.29 Hz, 1H), 9.87 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 185.80, 143.82, 138.91, 134.68, 134.28, 129.30, 128.58, 128.05, 124.76.

후처리

  1. washDouble elution by prep-TLC (10% heptane/DCM)

출처 및 근거

ORD 기록
ord-8d50f8ebc1114348be1a6893a5b8b862
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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