4-Methoxyphenol → HCID 12043575, compound

HRID 2303467Notes

Reaction equation

HRID 2303467 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.Cl[C:21]1[C:22]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][C:23]=2[S:24][C:25]=1[C:26]#[N:27]>CN(C=O)C>[CH3:35][S:32]([C:29]1[CH:30]=[CH:31][C:22]2[C:21]([O:19][C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)=[C:25]([C:26]#[N:27])[S:24][C:23]=2[CH:28]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11334762HCID 11334762, compound

Product 1

HCID 12043575HCID 12043575, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of KHMDS (0.18 g, 0.90 mmol) in DMF (7 mL) was treated by sequential addition of 4-methoxyphenol (0.12 g, 0.99 mmol) then 3-chloro-6-methanesulfonyl-benzo[b]thiophene-2-carbonitrile 8 (0.20 g, 0.75 mmol). After 2 h, the mixture was partitioned between EtOAc and brine. The organic layer was washed with brine (2×), dried (Na2SO4), filtered, and evaporated. Chromatography, followed by recrystallization (EtOAc/hexane) gave 0.20 g (74%) of 6-methanesulfonyl-3-(4-methoxy-phenoxy)-benzo[b]thiophene-2-carbonitrile 15 as white needles; (m+H)+ 360.

Workup

  1. customthe mixture was partitioned between EtOAc and brine
  2. washThe organic layer was washed with brine (2×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customChromatography, followed by recrystallization (EtOAc/hexane)

Sources & evidence

ORD record
ord-910bf3a4921e4f649221f70a97f864bc
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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