(2-Bromo-5-phenylthiophen-3-yl)methanol → 2-Bromo-5-phenylthiophene-3-carbaldehyde

HRID 590993Notes

Reaction equation

HRID 590993 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH2:7][OH:8]>ClCCl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[S:3][C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 70818445(2-Bromo-5-phenylthiophen-3-yl)methanol

Product 1

HCID 141138912-Bromo-5-phenylthiophene-3-carbaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2-bromo-5-phenylthiophen-3-yl)methanol (11e) (220 mg, 0.83 mmol) and manganese dioxide (720 mg, 8.3 mmol) in dichloromethane (3 mL) was stirred at room temperature for 160 minutes. The reaction mixture was filtered over Celite® and the filtrate was evaporated to dryness to provide the desired aldehyde (11f) (180 mg, 0.67 mmol, 81%), which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-397225a12090406a930f4564adc66fd2
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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