Bromine → HCID 97034606, compound

HRID 629173Notes

Reaction equation

HRID 629173 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([CH:10]=[O:11])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Br:12]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:12][C:6]1[CH:7]=[C:8]([CH:10]=[O:11])[S:9][C:5]=1[CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 202136665-(2-Methylpropyl)thiophene-2-carbaldehyde

Product 1

HCID 97034606HCID 97034606, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-isobutylthiophene-2-carbaldehyde (192 mg, 1.14 mmol) in 3 mL acetic acid at room temperature was added bromine (0.07 mL, 1.36 mmol). The resulting solution was stirred at room temperature in the dark for 48 h before being poured into 35 mL saturated sodium bicarbonate. Organics were extracted with ether (2×30 mL), dried with magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel (5% ethyl acetate in hexanes) to give 4-bromo-5-isobutylthiophene-2-carbaldehyde (147 mg, 52%). Used without further purification or characterization.

Workup

  1. extractionOrganics were extracted with ether (2×30 mL)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-98697053f4b2463584fa5b549df6d7f9
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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