Hydrochloric Acid → (4-Fluorophenyl)(2-thienyl)methanol

HRID 1645801Notes

Reaction equation

HRID 1645801 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][CH:12]=[C:11]1[CH:15]=[O:16].Cl>O1CCCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:15]([C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)[OH:16])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73642-ThiophenecarboxaldehydeHCID 99931-Bromo-4-fluorobenzeneHCID 5462224Magnesium

Product 1

HCID 10987480(4-Fluorophenyl)(2-thienyl)methanolYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred Grignard complex, previously prepared from 17.5 g (0.10 mol) 1-bromo-4-fluorobenzene and 2.43 g (0.10 mol) magnesium turnings in 50 ml tetrahydrofuran, 8.97 g (0.080 mol) thiophene-2-carboxaldehyde, dissolved in 30 ml tetrahydrofuran, was added dropwise. Upon complete addition the reaction mixture was refluxed for 1 h and then poured on a mixture of ice and 6N hydrochloric acid. Subsequent extraction with toluene, washing of the organic layer and evaporation in vacuo, gave 18 g of the desired (4-fluorophenyl)(2-thienyl)methanol as a brown oil. This was directly converted to the corresponding (4-fluorophenyl)(2-thienyl)methyl chloride with thionyl chloride by a procedure known to the art.

Workup

  1. additionwas added dropwise
  2. additionUpon complete addition the reaction mixture
  3. temperaturewas refluxed for 1 h
  4. extractionSubsequent extraction with toluene
  5. washwashing of the organic layer and evaporation in vacuo

Sources & evidence

ORD record
ord-98829cae6b0b486aafe6c30116c033d2
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

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