Triethylamine → 2-(Chloromethyl)-5-(4-(trifluoromethyl)phenyl)thiophene

HRID 1675308

Reaction equation

HRID 1675308 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH2:14]O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:14][C:12]1[S:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 219863522-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 575949792-(Chloromethyl)-5-(4-(trifluoromethyl)phenyl)thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 61.3 (45 mg, 0.18 mmol) in DCM (0.9 mL) were added triethylamine (24 μL, 0.18 mmol) and thionyl chloride (19 μL, 0.26 mmol) at room temperature. The mixture was stirred overnight and concentrated to afford 61.4. The crude product was used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-770aa0a6ed184a3e9e55631ad9668879
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Linked notes

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