Hydrogen Bromide → 7-Bromomethyl-4-chloroquinoline

HRID 1432860Notes

Reaction equation

HRID 1432860 reaction equation
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[BrH:14].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[Br:14][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22054610(4-Chloroquinolin-7-yl)methanol

Product 1

HCID 217084447-Bromomethyl-4-chloroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

7-Hydroxymethyl-4-chloroquinoline (0.2 g, 0.97 mmol) is treated with 48% HBr and heated to 120° C. for 1 hours. The resulting solution is cooled with ice, diluted with water and treated with ethyl acetate and sodium bicarbonate until basic to pH paper. The layers are separated and the organic layer is washed with water, dried (Na2SO4) and concentrated to give 7-bromomethyl-4-chloroquinoline (0.23 g, 0.9 mmol). MS m/z: M+=255; 1H NMR (CDCl3, 300 MHz) δ8.75 (d, 1H), 8.25 (d, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.5 (d, 1H), 4.7 (s. 2H).

Workup

  1. temperatureThe resulting solution is cooled with ice
  2. customThe layers are separated
  3. washthe organic layer is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e513432a62145fcb51534cc32fb97d8
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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