Bromide ion → HCID 57437551, compound

HRID 1986666Notes

Reaction equation

HRID 1986666 reaction equation
C(O[C:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[O:5])C.[Br-].S(=O)(=O)(O)O.[CH2:17](OCC)[CH3:18]>>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4]1([OH:5])[CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 76052Ethyl 2-thenoate

Product 1

HCID 57437551HCID 57437551, compound

Procedure

2.00 ml (14.88 mmol) ethylthiophene-2-carboxylate and 0.44 ml (1.45 mmol) titanium tetra-isopropyloxide are placed in 56 ml diethyl ether, 10.51 ml (31.54 mmol) ethylmagnesum bromide (Grignard reagent in tetrahydrofuran) in 28 ml diethyl ether are added dropwise within 1 hour, while the temperature should not rise above 20° C. The reaction mixture is stirred for 1.5 hours, then hydrolysed with 180 ml 10% sulphuric acid. The aqueous phase is extracted with diethyl ether, the combined organic phases are dried and evaporated to dryness. The residue is purified by chromatography. Yield: 0.300 g (14% of theoretical)

Workup

  1. customrise above 20° C
  2. extractionThe aqueous phase is extracted with diethyl ether
  3. customthe combined organic phases are dried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-807b0846fa7347d79a38ff3efd6e3166
Source dataset
uspto-grants-2009_06
Patent number
US07550472B2

Reaction notes

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