Hydrochloric Acid → 1-Chloro-3-(5-chlorobenzo[b]thiophen-3-yl)-propan-2-one

HRID 1671644Notes

Reaction equation

HRID 1671644 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][CH:7]=[C:8]([CH2:9][C:10]([OH:12])=O)[C:4]=2[CH:3]=1.C(Cl)(=O)[C:16]([Cl:18])=O.[N+](=C)=[N-].Cl>>[Cl:18][CH2:16][C:10](=[O:12])[CH2:9][C:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:5]=2[S:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 2050582-(5-Chloro-1-benzothiophen-3-yl)acetic acid

Product 1

HCID 161001811-Chloro-3-(5-chlorobenzo[b]thiophen-3-yl)-propan-2-oneYield 97.1%

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 5-chlorobenzo[b]thiophen-3-yl acetic acid (4.00 g, 17.6 mmol) with oxalyl chloride (1.7 mL, 2.5 g, 19 mmol), then ethereal diazomethane, then dry HCl gas. Work-up of the reaction mixture gave pure product as a light golden-yellow solid (4.43 g, 97% yield): 1H NMR (400 MHz, CDCl3) δ 4.12 (s, 2H) 4.15 (s, 2H) 7.35 (dd, J=8.6, 2.1 Hz, 1H) 7.43 (s, 1H) 7.65 (d, J=2.1 Hz, 1H) 7.79 (d, J=8.6 Hz, 1H).

Sources & evidence

ORD record
ord-91d17da6f1da4eb7814191fc26705a9e
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Reaction notes

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