Ammonium Chloride → (4-Bromo-thiophen-2-yl)-(4-ethyl-phenyl)-methanol

HRID 1625840Notes

Reaction equation

HRID 1625840 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([Mg]Br)=[CH:13][CH:12]=1)[CH3:10].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([C:14]2[CH:15]=[CH:16][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=2)[OH:8])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 877924-Bromothiophene-2-carbaldehydeHCID 178436501HCID 178436501, compound

Product 1

HCID 64307567(4-Bromo-thiophen-2-yl)-(4-ethyl-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2-thiophenecarboxaldehyde (4.78 g) in tetrahydrofuran (40 ml) was cooled to 0° C. under argon atmosphere, and thereto was added dropwise 4-ethylphenylmagnesium bromide (0.5 M tetrahydrofuran solution, 50 ml). The mixture was stirred at the same temperature for 30 minutes, and thereto was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-84:16) to give 4-bromo-2-thienyl-4-ethylphenylmethanol (5.37 g) as colorless oil. APCI-Mass m/Z 279/281 (M+H−H2O).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-84:16)

Sources & evidence

ORD record
ord-951cbda088d14a35879b746b7020b566
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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