ChemicalBook CAS DataBase List 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde

5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde synthesis

7synthesis methods

Product Name:5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
CAS Number:881674-56-2
Molecular formula:C11H8FNO
Molecular Weight:189.19

Synthesis of 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde: Using pyrrole as raw material, after being protected by N-alkylation of triisopropylsilyl chloride, it is then reacted with Vilsmeier reagent to obtain 1H-Pyrrole-3-carbaldehyde, which is then purified by N-bromosuccinimide (NBS) bromination and 2-fluorophenylboronic acid for Suzuki coupling reaction to obtain crude 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde, which was purified with toluene. The total yield was 35.5%.

1H-PYRROLE-3-METHANOL, 5-(2-FLUOROPHENYL)-

881674-58-4
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5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde

881674-56-2
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$6.00/250mg

Yield:881674-56-2 95.1%

Reaction Conditions:

with sodium bromate;sulfuric acid;bromine;sodium bromide in dichloromethane;water;butan-1-ol at 0 - 5; for 3.5 h;Solvent;

Steps:

1

Sodium bromate was added 52g (0.34mol) in a beaker, 400ml of water and dissolved with stirring, as a backup solution, the other solution of (5- (2-fluorophenyl) lH-pyrrol-3-yl) in a 3000 ml three-necked flask - methanol (6) 191g (1.0mol), dichloromethane 400ml, n-butanol 400ml, 35% sulfuric acid 20g (0.07mol), sodium bromide 1.2g, ice-salt bath to 0 ~ 5 , bromine was added dropwise sodium stock solution, an ice-salt bath after the addition stirring was continued for 3.5h, TLC detection starting material the reaction is completed, the reaction solution was transferred to a single neck flask, under reduced pressure to remove most of the organic solvent was concentrated under rotation, the precipitated yellow solid was cooled in a water bath with stirring 0.5h, yellow solid was collected by filtration, dried under reduced pressure to give 5- (2-fluorophenyl) lH-pyrrole-3-carbaldehyde 180g, (HPLC content: 98.4%), yield 95.1%.

References:

CN104356043,2016,B Location in patent:Paragraph 0020-0021

1240948-77-9 Synthesis