Hydrochloric Acid → HCID 131729542, compound

HRID 1686469Notes

Reaction equation

HRID 1686469 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9](O)[CH:8]=[C:7]([OH:12])[C:6]=1C)(=O)[CH3:2].[C:14](=O)([O-])[O-:15].[Cs+].[Cs+].[CH2:20]([S:22]([C:25]1[CH:30]=CC(F)=[C:27]([Cl:32])[CH:26]=1)(=[O:24])=[O:23])[CH3:21].Cl.CN1[C:39](=[O:40])[CH2:38]CC1>>[CH3:14][O:15][C:39](=[O:40])[CH2:38][C:9]1[CH:8]=[C:7]([OH:12])[CH:6]=[C:5]([O:4][C:1]2[CH:2]=[CH:30][C:25]([S:22]([CH2:20][CH3:21])(=[O:23])=[O:24])=[CH:26][C:27]=2[Cl:32])[CH:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 53420526HCID 53420526, compoundHCID 579047252-Chloro-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 131729542HCID 131729542, compound

Procedure

Methyl-3,5-dihydroxyphenyl acetate (0.20 g), cesium carbonate (1.08 g) and the product from example 3 step (i) in dry NMP were heated at 50° C. for 4 h. 2M HCl was added and extracted with ethyl acetate. The organics were dried (MgSO4) and evaporated under reduced pressure to a brown oil, which was purified by flash column chromatography (eluent 1:1 ethyl acetate/isohexane) to give a mixture of the mono- and bis-coupled products used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated under reduced pressure to a brown oil, which
  4. customwas purified by flash column chromatography (eluent 1:1 ethyl acetate/isohexane)
  5. customto give
  6. additiona mixture of the mono- and bis-coupled products
  7. customused in the next step without further purification

Sources & evidence

ORD record
ord-ae6b159e1acd42578a15e81ab4cebabe
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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