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ChemicalBook CAS DataBase List 6-Bromo-1-chloroisoquinoline
205055-63-6

6-Bromo-1-chloroisoquinoline synthesis

4synthesis methods
N-oxide 6-bromoisoquinoline (1.82 g, 8.12 mmol) was dissolved in dry DCM (80 mL), POCl3 (1.12 ml, 1.5 eq) was added dropwise at RT. The reaction was heated to 45°C for 2 hours. After cooling down the reaction to RT, DCM and excessive POCl3 were removed under the vacuum. The crude was re-dissolved into 100mL DCM and was washed by saturated Na2CO3, water and brine. The separated organic layer was dried over Na2SO4, and concentrated to give brown solid. The crude was purified by flash column using 2% MeOH in DCM to get the pale yellow solid 6-Bromo-1-chloroisoquinoline.
synthesis of 6-Bromo-1-chloroisoquinoline
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Yield:205055-63-6 62%

Reaction Conditions:

in ethyl acetate;trichlorophosphate

Steps:

90.A 6-Bromo-1-chloroisoquinoline
Example 90A 6-Bromo-1-chloroisoquinoline A solution of 6-bromo-1-hydroxy]isoquinoline (9.205 g, 41.0 mmol) in POCl3 (100 mL) was heated to 100° C. for 4 h. The reaction was concentrated to dryness. The residue was dissolved in ethyl acetate and the organic layer was washed with 5% NaHCO3, water, brine, dried over MgSO4 and concentrated. The residue was was chromatographed on silica gel eluding with CH2Cl2:hexane (3:7) to give the title compound (6.176 g, 62%). MS (DCI/NH3) m/z 241, 243 (M+1)+.

References:

Li, Qun;Woods, Keith W.;Zhu, Gui-Dong;Fischer, John P.;Gong, Jianchun;Li, Tongmei;Gandhi, Virajkumar;Thomas, Sheela A.;Packard, Garrick K.;Song, Xiaohong;Abrams, Jason N.;Diebold, Robert;Dinges, Jurgen;Hutchins, Charles;Stoll, Vincent S.;Rosenberg, Saul H.;Giranda, Vincent L. US2003/187026, 2003, A1

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