Hydrochloric Acid → HCID 19802560, compound

HRID 1645804Notes

Reaction equation

HRID 1645804 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].[S:10]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11]1.Cl>O1CCCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:15]([C:12]2[CH:13]=[CH:14][S:10][CH:11]=2)[OH:16])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 99931-Bromo-4-fluorobenzeneHCID 681353-ThiophenecarboxaldehydeHCID 5462224Magnesium

Product 1

HCID 19802560HCID 19802560, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred Grignard complex, previously prepared from 7.80 g (0.0446 mol) 1-bromo-4-fluorobenzene and 1.10 g (0.045 mol) magnesium turnings in 50 ml tetrahydrofuran, 5.00 g (0.0446 mol) thiophene-3-carboxaldehyde, dissolved in 50 ml tetrahydrofuran, was added dropwise. Upon completion of the addition, the reaction mixture was refluxed for 1 h and then poured on a mixture of ice and 6N hydrochloric acid. Subsequent extraction with dichloromethane, washing of the organic layer with water and evaporation in vacuo, left 8.50 g of crude (4-fluorophenyl)(3-thienyl)methanol as an oil. Chromatography on silica gel (THF/n-heptane 1:2 as eluent) gave 4.4 g of the pure (4-fluorophenyl)(3-thienyl)methanol, which was directly converted to the (4-fluorophenyl) (3-thienylmethyl chloride with thionyl chloride by a known procedure.

Workup

  1. additionwas added dropwise
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was refluxed for 1 h
  4. extractionSubsequent extraction with dichloromethane
  5. washwashing of the organic layer with water and evaporation in vacuo
  6. waitleft 8.50 g of crude (4-fluorophenyl)(3-thienyl)methanol as an oil

Sources & evidence

ORD record
ord-e09822a1d5264114b113c803d4dc4c47
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

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