Toluene → 2-(Chloromethyl)-4-phenylthiophene

HRID 1909886Notes

Reaction equation

HRID 1909886 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12]O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:23])=O>N1C=CC=CC=1>[Cl:23][CH2:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 12941349(4-Phenylthiophen-2-yl)methanol

Product 1

HCID 583066352-(Chloromethyl)-4-phenylthiophene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Phenyl thiophene-2-methanol (0.21 g), toluene (2.0 mL), and a catalytic amount of pyridine were added, and thionyl chloride (0.16 mL) was added dropwise thereto under ice-cooling. After stirring at room temperature for 3 hours, the reaction mixture was concentrated under reduced pressure, azeotroped with toluene, and dried at 60° C. under reduced pressure to obtain 2-(chloromethyl)-4-phenylthiophene (0.22 g).

Workup

  1. temperatureunder ice-cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-4e3358ab301a4978a0f11c11dcb5fe3c
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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