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

HRID 418608Notes

Reaction equation

HRID 418608 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 mixture. A precipitate formed, which was collected by filtration and washed with additional cold water. The material was dried under reduced pressure and used directly in the next step (crude product, >100% yield). MS (m/z): 415.1 (M+H)

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. temperaturecooled
  3. additioncarefully poured onto ice/water mixture
  4. customA precipitate formed
  5. filtrationwhich was collected by filtration
  6. washwashed with additional cold water
  7. customThe material was dried under reduced pressure

Sources & evidence

ORD record
ord-b6d06c63acf246e7a852f1c23fb0b277
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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