(3-Chloro-4-fluoro-benzo[b]thiophen-2-yl)methanol → 3-Chloro-4-fluoro-1-benzothiophene-2-carbaldehyde

HRID 2097047Notes

Reaction equation

HRID 2097047 reaction equation
[Cl:1][C:2]1[C:3]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]>C1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[C:3]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 59277586(3-Chloro-4-fluoro-benzo[b]thiophen-2-yl)methanol

Product 1

HCID 592775573-Chloro-4-fluoro-1-benzothiophene-2-carbaldehydeYield 88.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

A suspension of (3-chloro-4-fluoro-benzo[b]thiophen-2-yl)methanol (1.00 g, 4.63 mmol) and MnO2 (3.10 g, 35.2 mmol) in benzene (50 mL) was stirred at room temperature overnight. The solution was filtered through diatomaceous earth and the was filtrate was concentrated to give the title compound (880 mg, 87%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 10.32 (s, 1H), 7.63 (dd, J=8.2, 0.4 Hz, 1H), 7.50 (ddd, J=8.1, 8.1, 4.7 Hz, 1H), 7.13 (ddd, J=11.0, 7.9, 0.4 Hz, 1H).

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationthe was filtrate was concentrated

Sources & evidence

ORD record
ord-da154f16e43a450ab054c0ca5aa54686
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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