Hydrogen Bromide → 3-Bromoacetyl-5,6,7,8-tetrahydroisoquinoline

HRID 380561Notes

Reaction equation

HRID 380561 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)(=[O:3])[CH3:2].[BrH:14].BrBr>C(O)(=O)C>[Br:14][CH2:2][C:1]([C:4]1[N:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 154536993-Acetyl-5,6,7,8-tetrahydroisoquinoline

Product 1

HCID 154536983-Bromoacetyl-5,6,7,8-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-acetyl-5,6,7,8-tetrahydroisoquinoline (287.7 mg, 1.64 mmol) and hydrobromic acid (25% solution in acetic acid, 3.1 ml) was added a solution of bromine (93.3 μl, 1.81 mmol) in acetic acid (0.4 ml) at 0° C. The mixture was stirred at room temperature for an additional 3 h. and concentrated. The residue was made basic with saturated aqueous hydrogen bicarbonate and extracted with diethyl ether (150 ml). The organic layer dried (MgSO4) and concentrated to afford 524.9 mg of the crude title compound as an brown oil.

Workup

  1. concentrationconcentrated
  2. extractionextracted with diethyl ether (150 ml)
  3. dry with materialThe organic layer dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b7a1ac14f0443888c41aaf3edd7c721
Source dataset
uspto-grants-2001_10
Patent number
US06303628B1

Reaction notes

Loading…