Hydrochloric Acid → 4-(5-Bromothiophen-2-yl)benzaldehyde

HRID 1755501Notes

Reaction equation

HRID 1755501 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[Br:14]N1C(=O)CCC1=O.Cl>CN(C)C=O.CO>[Br:14][C:5]1[S:1][C:2]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimide2×HCID 7364994-(Thiophen-2-yl)benzaldehyde

Product 1

HCID 534263164-(5-Bromothiophen-2-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

In a two necked flask under argon, 0.75 g (3.98 mmol) of 4-(2-thienyl)benzaldehyde in 20 mL of dimethylformamide (DMF) are cooled to 0° C. 1.1 eq. (0.78 g, 4.38 mmol) of N-bromosuccinimide (NBS) are solubilised in a mixture of 10 mL of DMF and 10 mL of methanol. This solution of NBS (protected from light) is then added drop by drop (30 min) to the reaction medium. The temperature of the medium is then left to return to ambient temperature over 2 h. The medium is hydrolysed with a solution of 1 mol·L−1 HCl and extracted with ethyl ether. The combined organic phases are washed with a saturated NaCl solution then dried on anhydrous Na2SO4. After filtration and evaporation to dryness, the reaction mixture is recrystallised with acetone.

Workup

  1. waitThe temperature of the medium is then left
  2. extractionextracted with ethyl ether
  3. washThe combined organic phases are washed with a saturated NaCl solution
  4. dry with materialthen dried on anhydrous Na2SO4
  5. filtrationAfter filtration and evaporation to dryness
  6. customthe reaction mixture is recrystallised with acetone

Sources & evidence

ORD record
ord-2c268c4c319a452bb5849ab4d73bb79c
Source dataset
uspto-grants-2015_10
Patent number
US09171676B2

Reaction notes

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