Triethylamine → 2-(4-Butylphenyl)-5-(chloromethyl)thiophene

HRID 1675303Notes

Reaction equation

HRID 1675303 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([CH2:16]O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:16][C:14]1[S:15][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 59300633(5-(4-Butylphenyl)thiophen-2-yl)methanol

Product 1

HCID 593006792-(4-Butylphenyl)-5-(chloromethyl)thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 60.4 (40 mg, 0.16 mmol) in DCM (0.8 mL) were added triethylamine (23 μL, 0.16 mmol) and thionyl chloride (18 μL, 0.24 mmol) at room temperature. The mixture was stirred overnight and concentrated to afford 60.5. The crude product was used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-965249a64aa24e4eb78cdad023058a61
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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