Bromine → 5-Bromothiophene-2,3-dicarbaldehyde

HRID 61930Notes

Reaction equation

HRID 61930 reaction equation
[Br:1]Br.[S:3]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]1[CH:10]=[O:11]>C(Cl)(Cl)Cl>[Br:1][C:7]1[S:3][C:4]([CH:10]=[O:11])=[C:5]([CH:8]=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 573752Thiophene-2,3-dicarbaldehyde

Product 1

HCID 848194675-Bromothiophene-2,3-dicarbaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (6.0 mL, 116.3 mmol) was added drop wise at room temperature to a solution of 2,3-thiophenedicarboxaldehyde (5.1 g, 36.38 mmol) in 100 mL of CHCl3. The reaction mixture was stirred overnight and then excess bromine was quenched with a saturated solution of Na2S2O3. The organic layer was extracted with CHCl3, dried over Na2SO4 and volatiles were removed in vacuo to obtain 1 as a brown solid. Spectroscopically pure compound was isolated by column chromatography using silica gel as stationary phase and a 4:1 mixture of CH2Cl2:hexanes. 1H NMR (500 MHz, CDCl3): δ1 0.37 (s, 1H), 10.26 (s, 1H), 7.59 (s, 1H).

Workup

  1. customexcess bromine was quenched with a saturated solution of Na2S2O3
  2. extractionThe organic layer was extracted with CHCl3
  3. dry with materialdried over Na2SO4 and volatiles
  4. customwere removed in vacuo

Sources & evidence

ORD record
ord-d6483c3dd0e84ac2b3103bd2ca37c019
Source dataset
uspto-grants-2016_09
Patent number
US09444060B2

Reaction notes

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