Water → HCID 9843570, compound

HRID 1357983Notes

Reaction equation

HRID 1357983 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9953250HCID 9953250, compound

Product 1

HCID 9843570HCID 9843570, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-bromobenzyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (0.10 g, 0.25 mmol) in CH2Cl2 (15 mL) at 0° C. under nitrogen was added boron tribromide (1.47 mL, 1.47 mmol). The reaction was allowed to reach RT. After 8 hours, the reaction was poured into water (10 mL) and neutralized with saturated sodium bicarbonate. Additional CH2Cl2 (25 mL) was added, the organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was then chromatographed (SiO2, 2:1, hexanes/ethyl acetate) to provide the title compound (0.010 g, 10% yield): 1H NMR (CDCl3) 7.33 (d, 2H), 7.24 (dd, 2H), 6.97 (d, 1H), 6.88 (d, 2H), 6.80 (d, 2H), 6.75 (dd, 2H), 6.66 (m, 1H), 6.27 (s, 1H), 4.78 (t, 1H), 3.53 (m 2H), 3.13 (dd, 1H), 2.96 (m, 2H), 2.62 (m, 1H); ES-MS (m/z) 392 [M−H]−.

Workup

  1. customto reach RT
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then chromatographed (SiO2, 2:1, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fb65bfe978554900ad76d083876dade7
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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