Thionyl Chloride → 2-Bromo-6-[chloro(4-fluorophenyl)methyl]pyridine

HRID 2099561Notes

Reaction equation

HRID 2099561 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)O)[CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([Cl:19])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86602988HCID 86602988, compound

Product 1

HCID 860944222-Bromo-6-[chloro(4-fluorophenyl)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (6-bromopyridin-2-yl)(4-fluorophenyl)methanol in CH2Cl2 (120 mL) @ 0° C. was added SOCl2 (5.870 g, 49.34 mmol). The mixture was allowed to slowly warm to rt and stirred for 16 hr. The mixture was cooled back to 0° C. and quenched with saturated aqueous NaHCO3. The resulting mixture was extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (20-30% CH2Cl2 in Hexanes) to give 2-bromo-6-[chloro(4-fluorophenyl)methyl]pyridine. 1H NMR (500 MHz, CDCl3) δ 7.58 (t, 1H, J=7.7), 7.51 (d, 1H, J=7.6), 7.47-7.39 (m, 3H), 7.04 (t, 2H, J=8.7), 6.08 (s, 1H), LRMS m/z (M+H) Calcd.: 300.0, found: 300.0.

Workup

  1. temperatureThe mixture was cooled back to 0° C.
  2. customquenched with saturated aqueous NaHCO3
  3. extractionThe resulting mixture was extracted 3× with CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel chromatography (20-30% CH2Cl2 in Hexanes)

Sources & evidence

ORD record
ord-fd02a1bf418143008d48467711238077
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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