Toluene → 2-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester

HRID 1914540Notes

Reaction equation

HRID 1914540 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][CH:18]=1)=[O:13])[CH3:10].C1(C)C=CC=CC=1>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][C:18]=1[Br:1])=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 58110324Ethyl 5-phenylthiophene-3-carboxylate

Product 1

HCID 581102722-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl esterYield 56.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Bromosuccinimide (1.22 g, 6.83 mmol) was added to a solution of ethyl-2-phenylthiophen-4-carboxylate (6.83 mmol) in acetic acid (10 mL) and stirred overnight. Toluene was added and the solvent was removed under vacuum. The product was purified by flash chromatography on silica, eluting with 0%-10% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (1.2 g). LCMS m/z 312.52 [M+H]+ R.T.=4.55 mins (Analytical Method 5).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe product was purified by flash chromatography on silica
  3. washeluting with 0%-10% ethyl acetate in cyclohexane
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-90eec9a2808348f4a8dd4a7d5f6a494f
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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