1,3-Dibromobenzene → 3-Bromophenyl-5-ethyl-2-thienylmethanol

HRID 1625767Notes

Reaction equation

HRID 1625767 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.[CH2:14]([C:16]1[S:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1)[CH3:15].[Cl-].[NH4+]>O1CCCC1>[Br:8][C:4]1[CH:3]=[C:2]([CH:21]([C:19]2[S:20][C:16]([CH2:14][CH3:15])=[CH:17][CH:18]=2)[OH:22])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 79271,3-DibromobenzeneHCID 25517Ammonium ChlorideHCID 1698305-Ethyl-2-thiophenecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 611008623-Bromophenyl-5-ethyl-2-thienylmethanolYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dibromobenzene (3.7 g) in tetrahydrofuran (25 ml) was cooled to −78° C. under argon atmosphere, and thereto was added dropwise n-butyl lithium (2.44 M hexane solution, 5.55 ml). The reaction mixture was stirred at the same temperature for 10 minutes, and thereto was added dropwise a solution of 5-ethyl-2-thiophenecarboxaldehyde (2.0 g) in tetrahydrofuran (10 ml). The mixture was stirred at the same temperature for 30 minutes, and thereto was added a saturated ammonium chloride solution, and the reaction mixture was warmed to room temperature. The mixture was extracted with ethyl acetate, and the extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-85:15) to give 3-bromophenyl-5-ethyl-2-thienylmethanol (2.97 g) as a pale yellow syrup. APCI-Mass m/Z 279/281 (M+H−H2O).

Workup

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extract was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-85:15)

Sources & evidence

ORD record
ord-1edaaae7da114f578cfb77a5432c825f
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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