Dichloromethane → 2-(5-Cyanothien-2-yl)anisole

HRID 852212

Reaction equation

HRID 852212 reaction equation
Br[C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O1CCOCC1.O>[C:7]([C:5]1[S:6][C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])=[CH:3][CH:4]=1)#[N:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 35950595-Bromothiophene-2-carbonitrile

Product 1

HCID 220385512-(5-Cyanothien-2-yl)anisoleYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-bromothiophene-2-carbonitrile (1.25 g, 6.65 mmol) in 50 ml of dioxane is degassed with argon, tetralkis(triphenylphosphine)palladium(0) (768 mg, 0.665 mmol) is added and the mixture is stirred for 5 minutes. 2-Methoxybenzene boronic acid (2.02 g, 13.3 mmol) and aqueous 2 N sodium carbonate (13.3 ml) are successively added and the mixture is stirred for 16 hours at 85° C. Extractive work-up (2×50 ml dichloromethane and 2×30ml water). The organic phase is dried over sodium sulfate, filtrated and evaporated. The residue (4.05 g) is purified via flash chromatography on silica (eluent: 100% hexane>hexane/ethyl acetate 96:4 gradient) to give 1.37 g of 2-(5-cyanothien-2-yl)anisole (96%). M+=215.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 16 hours at 85° C
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe residue (4.05 g) is purified via flash chromatography on silica (eluent: 100% hexane>hexane/ethyl acetate 96:4 gradient)

Sources & evidence

ORD record
ord-1c9d1ab54b2e4d29be8a251b3bcdf72f
Source dataset
uspto-grants-2007_08
Patent number
US07253181B2

Linked notes

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