Potassium Carbonate → 2-(2-Bromothiophen-3-yl)ethan-1-ol

HRID 2267339Notes

Reaction equation

HRID 2267339 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10]1.[Al].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl.Cl(O)(=O)(=O)=O>[Br:1][C:10]1[S:9][CH:13]=[CH:12][C:11]=1[CH2:14][CH2:15][OH:16]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 83731Thiophene-3-ethanolHCID 5359268Aluminum

Product 1

HCID 193595722-(2-Bromothiophen-3-yl)ethan-1-olYield 64%

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (33.8 g, 0.19 mmol) followed by perchloric acid (0.19 g, 0.002 mol) were added to a solution of 2-(thiophen-3-yl)ethanol)24.3 g, 0.19 mol) in carbon tetrachloride (250 mL) in a flask wrapped with aluminum foil at rt. The mixture was stirred in the dark at rt overnight and then potassium carbonate (40 g) was added. After stirring at rt for 1 h the mixture was filtered through Celite and washed with diethyl ether. The solvent was removed in vacuo and the product purified by flash chromatography eluting with ethyl acetate/hexane ((1:3) to give the title compound as an oil (25 g, 64%). MS (M+H)+ 207/209.

Workup

  1. stirringAfter stirring at rt for 1 h the mixture
  2. filtrationwas filtered through Celite
  3. washwashed with diethyl ether
  4. customThe solvent was removed in vacuo
  5. customthe product purified by flash chromatography
  6. washeluting with ethyl acetate/hexane ((1:3)

Sources & evidence

ORD record
ord-06f6982627e84416b8f3df45906d6b74
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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