Hydrochloric Acid → HCID 68769857, compound

HRID 1171437Notes

Reaction equation

HRID 1171437 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[I:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([OH:18])[CH:9]=1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CN(C=O)C>[I:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromide2×HCID 10796Cesium carbonate2×HCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 68769857HCID 68769857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of caesium carbonate (35.2 g, 108 mmol), methyl 4-iodo-2-hydroxybenzoate (25 g, 90 mmol), phenethyl bromide (16 ml, 117 mmol) in DMF (500 ml) is stirred for 10 hours at room temperature. Caesium carbonate (20 g, 61.4 mmol) and phenethyl bromide (8.5 ml, 61.4 mmol) are added to the suspension. The organic phase is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl ether. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator.

Workup

  1. extractionThe desired product is extracted by addition of ethyl ether
  2. washThe organic phase is washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-90ab9d4608db46c2bafa913aa16ea33d
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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