Phosphorus oxychloride → 2-Bromo-4-chlorothieno(3,2-c)pyridine

HRID 549282Notes

Reaction equation

HRID 549282 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[S:15][C:14]2[CH:13]=[CH:12][NH:11][C:10](=O)[C:9]=2[CH:8]=1>>[Br:6][C:7]1[S:15][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([Cl:3])[C:9]=2[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 128758932-bromothieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 177503902-Bromo-4-chlorothieno(3,2-c)pyridineYield 80.7%

Conditions

Temperature
135 °C

Procedure

Phosphorus oxychloride (4.08 g, 26.6 mmol) was added dropwise to 2-bromothieno[3,2-c]pyridin-4 (5H)-one (2.04 g, 8.87 mmol) at 0° C. The mixture was heated at 135° C. for 2.5 h, then carefully poured over ice water. The precipitated was collected by filtration and dried to yield 1.78 g (80.7%) of title product. 1H NMR (270 MHz, CH3OH-d4) δ ppm 7.67 (d, 1H) 7.88 (dddd, J=6.33 Hz, 2H) 8.19 (d, J=5.54 Hz, 1H); MS 248.0 (M−H)+; Purity (HPLC) 100

Workup

  1. filtrationThe precipitated was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-fc7fa77ce712466ca5544b58c2148a5f
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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