Iodine → Benzo[b]thiophen-7-yl-p-tolylmethanol

HRID 15408

Reaction equation

HRID 15408 reaction equation
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Mg].II.[CH3:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH:19]([C:18]3[CH:21]=[CH:22][C:15]([CH3:14])=[CH:16][CH:17]=3)[OH:20])[C:7]1=2

Participants

7

Reactant 5

HCID 807IodineHCID 77254-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 120455387-Bromobenzo[b]thiophene

Product 1

HCID 68717781Benzo[b]thiophen-7-yl-p-tolylmethanolYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared using 7-bromobenzo-[b]thiophene (1.0 g), magnesium (0.13 g), a catalytic amount of iodine and tetrahydrofuran (3 mL) according to the general method. To the Grignard reagent solution was added a solution of 4-methylbenzaldehyde (0.62 g) in tetrahydrofuran (5 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred at room temperature overnight and a saturated ammonium chloride aqueous solution was added to the mixture. The mixture was extracted with diethyl ether, and the organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1) gave the title compound (0.68 g) as yellow oil.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washthe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  6. customFurther purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-791f4186fc2a410a8b3514d9786fd950
Source dataset
uspto-grants-2010_06
Patent number
US07732596B2

Linked notes

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