Boron tribromide → HCID 66788883, compound

HRID 576119Notes

Reaction equation

HRID 576119 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19]C)=[CH:16][CH:17]=3)[CH2:12][N:11]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])(=[O:23])=[O:22])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[CH2:12][N:11]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])(=[O:23])=[O:22])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66787988HCID 66787988, compound

Product 1

HCID 66788883HCID 66788883, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of 4-(3,4-dichlorophenyl)-7-methoxy-2-(2-nitrophenylsulfonyl)-1,2,3,4-tetrahydroisoquinoline (3.39 g, 6.88 mmol) in dichloromethane (70 mL) was added boron tribromide (3.25 mL, 34.4 mmol) drop wise. The mixture was stirred for 5 minutes and then warmed to 0° C. for 1 hour. The mixture was quenched with water slowly and then the aqueous layer was extracted with dichlormethane (2×). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 4-(3,4-dichlorophenyl)-2-(2-nitrophenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-ol (3.25 g, 98%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.80 (dd, J=8.0, 1.2 Hz, 1H), 7.67-7.63 (m, 1H), 7.58 (dd, J=7.9, 1.2 Hz, 1H), 7.54-7.50 (m, 1H), 7.16 (d, J=8.3 Hz, 1H), 7.02 (d, J=2 Hz, 1H), 6.86 (dd, J=8.3, 2 Hz, 1H), 6.77 (d, J=8.2 Hz, 1H), 6.68-6.65 (m, 2H), 4.88 (s, 1H), 4.74 (d, J=16.2 Hz, 1H), 4.53 (d, J=16.1 Hz, 1H), 4.16 (dd, J=4.9, 4.9 Hz, 1H), 3.83 (dd, J=13.2, 4.5 Hz, 1H), 3.62 (dd, J=13.1, 5.5 Hz, 1H).

Workup

  1. customThe mixture was quenched with water slowly
  2. extractionthe aqueous layer was extracted with dichlormethane (2×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4389a1f11cc547d9bea655ea2daebb33
Source dataset
uspto-grants-2015_05
Patent number
US09034899B2

Reaction notes

Loading…