{3-Bromothieno[2,3-b]pyridin-2-yl}methanol → 3-Bromothieno[2,3-b]pyridine-2-carbaldehyde

HRID 591006Notes

Reaction equation

HRID 591006 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH2:11][OH:12]>ClCCl.[O-2].[Mn+2]>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 70855402{3-Bromothieno[2,3-b]pyridin-2-yl}methanol

Product 1

HCID 823872043-Bromothieno[2,3-b]pyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of {3-bromothieno[2,3-b]pyridin-2-yl}methanol (14c) (394 mg, 1.61 mmol) and manganese (II) oxide (1.4 g, 16.1 mmol) in dichloromethane (10 mL) was stirred for 20 hours, filtrated and evaporated to dryness to give the desired aldehyde (14d) without further purification (270 mg, 1.12 mmol, 70%).

Workup

  1. filtrationfiltrated
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-191ed37298734886a2d09e97eaf0f626
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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