Triethylamine → 2-(Chloromethyl)-3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene

HRID 1675316Notes

Reaction equation

HRID 1675316 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH2:14]O)=[C:11]([CH3:16])[CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.S(Cl)([Cl:28])=O>C(Cl)Cl>[Cl:28][CH2:14][C:12]1[S:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)=[CH:10][C:11]=1[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 21986444[3-Methyl-5-(4-trifluoromethylphenyl)thien-2-yl]methanol

Product 1

HCID 159462812-(Chloromethyl)-3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 62.6 (63 mg, 0.23 mmol) in DCM (2.3 mL) were added triethylamine (32 μL, 0.23 mmol) and thionyl chloride (25 μL, 0.35 mmol) at room temperature. The mixture was stirred overnight and concentrated to afford 62.7. The crude product was used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-cfedaa58355d466b95abaef9c1ba0e3d
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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