Thionyl Chloride → 2-(4-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

HRID 500774Notes

Reaction equation

HRID 500774 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=3)[S:13][C:6]=12.O=S(Cl)[Cl:31]>>[Cl:31][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=3[F:1])[CH:11]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59457734HCID 59457734, compound

Product 1

HCID 594245202-(4-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridineYield 100%

Procedure

The alcohol 51 (880 mg, 2.22 mmol) was suspended in SOCl2 (10 ml) and the reaction mixture was refluxed for 1 hour, cooled and carefully poured onto ice/water. A precipitate was formed which was collected by filtration, washed with additional cold water and dried under vacuum to afford the title compound 52 (919 mg, 100% yield), which was used without additional purification. MS (m/z): 415.1(100%) (M+H), 417.1 (36%) (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. temperaturecooled
  3. additioncarefully poured onto ice/water
  4. customA precipitate was formed which
  5. filtrationwas collected by filtration
  6. washwashed with additional cold water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c852774be75549fc898e9564cabbb62c
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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