Sodium Carbonate → HCID 86671493、化合物

HRID 536610

反応式

HRID 536610 の反応式
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[CH:8]=[O:9].[OH:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:7][C:6]1[C:2]([C:14]2[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=2)=[C:3]([CH:8]=[O:9])[S:4][CH:5]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 125595283,4-Dibromothiophene-2-carbaldehyde2 回

生成物 1

HCID 86671493HCID 86671493、化合物収率 17%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 86587398Ethanol toluene water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3,4-dibromothiophene-2-carbaldehyde (see Intermediate 1 (see Example 15 for Intermediate synthesis)) (2.0 g, 7.5 mmol), 4-hydroxyphenylboronic acid (Scheme II, 8A, X1=4-hydroxyphenyl) (1.0 g, 7.5 mmol), Na2CO3 (1.6 g, 15 mmol), and Pd(PPh3)4 (431 mg, 0.37 mmol) in toluene/EtOH/H2O (30 mL, 5:3:2) was heated to 80° C. and stirred overnight under nitrogen. When TLC indicated that the starting material was consumed, the mixture was diluted with water, neutralized to pH=4-5 with HCl (1M), extracted with EtOAc, concentrated, and purified by column chromatography (PE:EtOAc=20:1) to give 4-bromo-3-(4-hydroxyphenyl)thiophene-2-carbaldehyde (Scheme II, 8, X1=4-hydroxyphenyl) (350 mg, yield 17%) as a white solid. 1H NMR (DMSO-d6 400 MHz): δ9.90 (s, 1H), 9.53 (s, 1H), 8.33 (s, 1H), 7.33 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.4 Hz, 2H).

後処理

  1. customwas consumed
  2. additionthe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationconcentrated
  5. custompurified by column chromatography (PE:EtOAc=20:1)

出典と根拠

ORDレコード
ord-921792d5865d4682be7401a285764e34
出典データセット
uspto-grants-2014_10
特許番号
US08859611B2

関連ノート

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