5-CHLORO-2,3-DIHYDRO-BENZOFURAN-3-YLAMINE HYDROCHLORIDE synthesis

6synthesis methods

Product Name:5-CHLORO-2,3-DIHYDRO-BENZOFURAN-3-YLAMINE HYDROCHLORIDE
CAS Number:669-45-4
Molecular formula:C8H9Cl2NO
Molecular Weight:206.0692

Benzofuran, 3-azido-5-chloro-2,3-dihydro-

1243205-05-1
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5-CHLORO-2,3-DIHYDRO-BENZOFURAN-3-YLAMINE HYDROCHLORIDE

669-45-4
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$90.00/50mg

Yield:669-45-4 92%

Reaction Conditions:

Stage #1: 3-azido-5-chloro-2,3-dihydro-1-benzofuranwith triphenylphosphine in tetrahydrofuran;water at 50;Inert atmosphere;
Stage #2: with hydrogenchloride in tetrahydrofuran;1,4-dioxane;water at 20; for 0.0833333 h;Inert atmosphere;

Steps:

6

To a solution of 3-azido-5-chloro-2,3-dihydrobenzofuran (6.10 g, 31.3 mmol) in THF (260 ml_) were sequentially added water (5.63 ml_) and triphenylphosphine (24.7 g, 94 mmol). The reaction was stirred at 50 ⁰C overnight, whereupon it was allowed to cool to room temperature and diluted with Et₂O (500 ml_). HCI (4 N) in dioxane (8.25 ml_, 33 mmol) was added and the solution was stirred for 5 min at room temperature, whereupon the precipitate was collected by filtration to afford the title compound as a white solid. Yield = 5.9 g, 28.9 mmol, 92%.

References:

WO2010/100606,2010,A1 Location in patent:Page/Page column 57