ChemicalBook CAS DataBase List 5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline

5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline synthesis

4synthesis methods

Product Name:5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline
CAS Number:1203684-57-4
Molecular formula:C11H14BrN
Molecular Weight:240.14

5-bromo-4,4-dimethyl-3,4-dihydroisoquinoline-1(2H)-one

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5-broMo-4,4-diMethyl-1,2,3,4-tetrahydroisoquinoline

1203684-57-4
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Yield:1203684-57-4 0.8 g

Reaction Conditions:

Stage #1: 5-bromo-4,4-dimethyl-3,4-dihydroisoquinoline-1(2H)-onewith dimethylsulfide borane complex in tetrahydrofuran at 0; for 19 h;Reflux;
Stage #2: with methanol for 18 h;Reflux;

Steps:

103D 5-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

To a solution of 103C (1.0 g, 3.93 mmol) in dry THF (10 mL) at 0 °C, was added borane-dimethyl sulfide complex (1.12 mL, 11.81 mmol), the reaction mixture was slowly brought to rt, stirred for 1 h and then heated to reflux for 18 h. The solvent was removed and the residue was quenched with MeOH and heated to reflux for 18 h. The solvent was removed and the residue was dissolved in EtOAc, washed with H₂O, brine, dried (Na₂S0₄), filtered and concentrated to give 0.8 g of 103D as a white solid. The material was carried onto the next step without further purification. MS (ESI) m/z: 240.0 (M+H)⁺.

References:

WO2013/56034,2013,A1 Location in patent:Paragraph 003606

71095-49-3 Synthesis