Hydrochloric Acid → HCID 28639788, compound

HRID 1778695Notes

Reaction equation

HRID 1778695 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.Cl[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenolHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 28639788HCID 28639788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction mixture of 4-bromo-2-methylphenol (Aldrich, Cat. No. 681121) (0.50 g, 2.7 mmol), 2-chloro-N,N-dimethylacetamide (Aldrich, Cat. No. 24350) (0.27 mL, 2.7 mmol) and potassium carbonate (1.1 g, 8.0 mmol) in DMF (4 mL) was stirred at 60° C. overnight. After cooling to r.t., the mixture was adjusted to pH˜2 with aqueous HCl, and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the product which was directly used in nest step reaction without further purification. LCMS (M+H)+=272.2/274.2.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the product which
  6. customwas directly used in nest step reaction without further purification

Sources & evidence

ORD record
ord-00df84aad84b4400bbd10fce70253f37
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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