(3-Chloro-7-fluoro-benzo[b]thiophen-2-yl)methanol → 3-Chloro-7-fluoro-benzo[b]thiophene-2-carbaldehyde

HRID 1362305Notes

Reaction equation

HRID 1362305 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[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[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 59277539(3-Chloro-7-fluoro-benzo[b]thiophen-2-yl)methanol

Product 1

HCID 592775543-Chloro-7-fluoro-benzo[b]thiophene-2-carbaldehydeYield 102.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

A suspension of (3-chloro-7-fluoro-benzo[b]thiophen-2-yl)methanol (600 g, 2.78 mmol) and MnO2 (1.69 g, 19.5 mmol) in benzene (25 mL) was stirred at room temperature for 2 d. The solution was filtered through diatomaceous earth and the filtrate concentrated to give the title compound (610 mg, quantitative) as a light, yellow solid: 1H NMR (300 MHz, CDCl3) δ 10.35 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.51 (ddd, J=8.0, 8.0, 4.8 Hz, 1H), 7.32-7.26 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-123ffa9e27be41f4b8e21e68899e3ec7
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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