Hydrochloric Acid → 2-Propanone, 1-chloro-3-(3-thienyl)-

HRID 2375567Notes

Reaction equation

HRID 2375567 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.C(Cl)(=O)[C:11]([Cl:13])=O.[N+](=C)=[N-].Cl>>[Cl:13][CH2:11][C:7](=[O:9])[CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 234043-Thiophenacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 161001782-Propanone, 1-chloro-3-(3-thienyl)-Yield 100%

Procedure

The procedure described above for the synthesis of 1-chloro-3-[2-(3-methylbenzo[b]thiophen-2-yl)propan-2-one was followed, reacting thiophene-3-acetic acid (5.32 g, 37.4 mmol) with oxalyl chloride (3.6 mL, 5.2 g, 41 mmol, then ethereal diazomethane, then dry HCl gas. Work-up gave pure product, a brown oil which solidified upon refrigeration to a golden-brown, waxy solid (6.52 g, 100% yield): 1H NMR (400 MHz, CDCl3) δ 3.94 (s, 2H) 4.13 (s, 2H) 6.99 (d, J=5.1 Hz, 1H) 7.16 (dd, J=1.5, 0.8 Hz, 1H) 7.33 (dd, J=4.9, 2.9 Hz, 1H).

Workup

  1. customWork-up gave pure product

Sources & evidence

ORD record
ord-1db9982599f24957b1822be37e286c20
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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