Potassium Iodide → HCID 68840106, compound

HRID 238889Notes

Reaction equation

HRID 238889 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]=1[OH:14])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.[I-].[K+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]=1[O:14][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=1)=[O:4]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 68844599HCID 68844599, compound

Product 1

HCID 68840106HCID 68840106, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

200 mg 7-Hydroxy-benzo[b]thiophene-6-carboxylic acid methyl ester, 313 mg cesium carbonate, 230 mg of 1-bromomethyl-4-trifluoromethyl-benzene and 32 mg potassium iodide were dissolved in 1 ml of N,N-dimethylformamide and stirred for 3 h at 60° C. 10 ml of ethyl acetate and 10 ml of brine were added to the reaction. The organic layer was separated and washed again with 10 ml of brine. It was then dried over sodium sulphate, filtered and concentrated in vacuo to afford 325 mg of 7-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-6-carboxylic acid methyl ester.

Workup

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of brine
  3. dry with materialIt was then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1403f43389c845abab22bb73d7d3a86b
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

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