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

HRID 2235655Notes

Reaction equation

HRID 2235655 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-9f7b1846c959464b92b04f8021d2c76a
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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