Sodium Carbonate → HCID 23103382, compound

HRID 1012027Notes

Reaction equation

HRID 1012027 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:15]([C:17]2[S:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]=2[CH3:22])O)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:17]1[S:18][C:19]2[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=2[C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 67186585HCID 67186585, compound

Product 1

HCID 23103382HCID 23103382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 1.56 M hexane (23.7 ml) of n-butyl lithium was added dropwise to a solution of 3-methyl-1-benzothiophene (5.0 g) in tetrahydrofuran (50 ml) at −78° C. under an argon atmosphere, and the mixture was stirred for half an hour at the same temperature. Then, a solution of 3-bromobenzaldehyde (6.05 g) in tetrahydrofuran (6 ml) was added dropwise to the mixture, and the mixture was stirred for half an hour. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous solution of saturated ammonium chloride and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (3-bromophenyl)(3-methyl-1-benzothien-2-yl)methanol (10.0 g) as achromatic oily matter. Borontrifluoride diethyl ether complex (4.42 ml) and triethylsilane (9.58 ml) were added to a solution of (3-bromophenyl)(3-methyl-1-benzothien-2-yl)methanol in dichloromethane (100 ml) at −30° C., and the mixture was stirred for half an hours. After the reaction mixture was heated to −10° C. and stirred for 10 minutes, aqueous solution of saturated sodium carbonate was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue, and the residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 2-(3-bromobenzyl)-3-methyl-1-benzothiophene (6.68 g).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated from the filtrate under reduced pressure
  7. customto give the residue
  8. customthe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a77700356faf432bbaf67d870ddd175d
Source dataset
uspto-grants-2011_07
Patent number
US07977466B2

Reaction notes

Loading…