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

HRID 1362301Notes

Reaction equation

HRID 1362301 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 diatamaceous 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 diatamaceous earth
  2. concentrationthe was filtrate was concentrated

Sources & evidence

ORD record
ord-2bd3e9719110411c8ad266b9e4afe814
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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