Boron tribromide → HCID 9966722, compound

HRID 397089Notes

Reaction equation

HRID 397089 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)[N:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:19][C:16]1[CH:15]=[CH:14][C:13]([CH:9]2[C:10]3[C:5](=[CH:4][C:3]([OH:2])=[CH:12][CH:11]=3)[CH2:6][CH2:7][N:8]2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 30246236-Methoxy-1-(4-methoxyphenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 9966722HCID 9966722, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 6-methoxy-1-(4-methoxy-phenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline (0.075 g, 0.217 mmol, 1.0 eq.) in CH2Cl2 (3 ml) cooled to −78° C. under an atmosphere of N2 was added BBr3 as a 1.0 M solution in CH2Cl2 (0.65 ml, 0.65 mmol, 3.0 eq.). The reaction was stirred overnight, slowly allowing the reaction mixture to warm to rt. The reaction was quenched with MeOH (2 ml) and stirring was continued for 1 hour. The mixture was diluted with EtOAc (20 ml), water (2 ml), and sat. NaHCO3 (2 ml, until the pH of the aqueous layer was approximately 8). The layers were separated and the aqueous layer diluted with water (10 ml), then extracted with EtOAc (2×20 ml) and CH2Cl2 (2×20 ml). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to flash chromatography (SiO2, hexanes:EtOAc 3:2) to give the desired compound (0.053 g, 0.167 mmol, 77% yield).

Workup

  1. customThe reaction was quenched with MeOH (2 ml)
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. additionThe mixture was diluted with EtOAc (20 ml), water (2 ml), and sat. NaHCO3 (2 ml
  5. customThe layers were separated
  6. additionthe aqueous layer diluted with water (10 ml)
  7. extractionextracted with EtOAc (2×20 ml) and CH2Cl2 (2×20 ml)
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3569431ee7cc45e49a43a6537c94438a
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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