Boron tribromide → HCID 9834670, compound

HRID 853789Notes

Reaction equation

HRID 853789 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1)[CH2:11][CH2:10]2>C(Cl)Cl>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([N:12]2[CH2:11][CH2:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([OH:6])[CH:8]=3)[CH2:13]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69475863HCID 69475863, compound

Product 1

HCID 9834670HCID 9834670, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 1.0 M solution of boron tribromide in CH2Cl2 (0.54 mL) was added dropwise to a cooled (−15° C.) solution of 6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (0.036 g) in CH2Cl2 (1.4 mL). After 30 min the reaction was warmed to room temperature. After 2 h the reaction was diluted with CH2Cl2 (30 mL) and washed successively with saturated aqueous sodium bicarbonate (2×20 mL) and saturated aqueous sodium chloride (1×15 mL). The organic extract was dried and evaporated. The resulting residue was purified by chromatography on silica gel (eluant; a gradient of 0 to 20% methanol in dichloromethane) to give the title compound (0.026 g); MS: 242.0 (MH+); HPLC tR: 0.46 min; 1H NMR (DMSO-d6): 9.14 (s, 1H), 8.79 (s, 1H), 6.94 (d, 1H, J=6 Hz), 6.85 (d, 2H, J=6.65 (d, 2H J=9 Hz), 6.56 (d, 1H, J=6 Hz), 6.52 (s, 1H), 4.06.(s, 2H), 3.28 (t, 2H, J=6 Hz), 2.78 (t, 2H, J=6 Hz).

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate (2×20 mL) and saturated aqueous sodium chloride (1×15 mL)
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated
  5. customThe resulting residue was purified by chromatography on silica gel (eluant

Sources & evidence

ORD record
ord-5d5370e278ea463dbed867448bea1f0b
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

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