Benzoyl Peroxide → 3-Bromo-7-(bromomethyl)-4-chlorothieno[3,2-c]pyridine

HRID 2390644Notes

Reaction equation

HRID 2390644 reaction equation
[Br:1][C:2]1[C:6]2[C:7]([Cl:12])=[N:8][CH:9]=[C:10]([CH3:11])[C:5]=2[S:4][CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:1][C:2]1[C:6]2[C:7]([Cl:12])=[N:8][CH:9]=[C:10]([CH2:11][Br:20])[C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 184507713-Bromo-4-chloro-7-methylthieno[3,2-c]pyridine

Product 1

HCID 184507883-Bromo-7-(bromomethyl)-4-chlorothieno[3,2-c]pyridine

Procedure

A solution of Example 277C (1 g, 3.81 mmol) in CCL (30 mL) was treated with NBS (0.755 g, 4.24 mmol) and benzoyl peroxide (0.093 g, 0.38 mmol), heated to reflux for 24 hours, cooled to room temperature, and filtered. The filtrate was concentrated to provide 3-bromo-7-(bromomethyl)-4-chlorothieno[3,2-c]pyridine, which was used directly. MS (ESI(+)) m/e 339.5, 341.6, 343.4 (M+H)+. The crude product was dissolved in DME (7.5 mL), treated with sodium acetate (1.6 g, 19.5 mmol), heated to 100° C. overnight, and partitioned between water and ethyl acetate. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography with 10% ethyl acetate/hexanes to provide 0.65 g (53% yield) of the desired product. MS (ESI(+)) m/e 319.7, 321.7, 323.7 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f29459f72d074c48b72c702ec064325d
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

Loading…