Hydrochloric Acid → 1-(4-((4-(Bromomethyl)benzyl)oxy)-3-chloro-2-hydroxyphenyl)ethanone

HRID 1161175

Reaction equation

HRID 1161175 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[C:9]([OH:18])=[C:10]([C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][C:13]=1[OH:14].[Br:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Br)=[CH:23][CH:22]=1.Cl>CC(C)=O.CCOC(C)=O>[Br:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:14][C:13]2[CH:12]=[CH:11][C:10]([C:15](=[O:17])[CH3:16])=[C:9]([OH:18])[C:8]=2[Cl:7])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 693351,4-Bis(bromomethyl)benzeneHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanone

Product 1

HCID 574384161-(4-((4-(Bromomethyl)benzyl)oxy)-3-chloro-2-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add K2CO3 (1.48 g, 10.7 mmol) to a solution of 1-(3-chloro-2,4-dihydroxy-phenyl)ethanone (2.00 g, 10.7 mmol) and 1,4-bis(bromomethyl)benzene (2.83 g, 10.7 mmol) in acetone (100 mL). Cool and work up with a 10% HCl solution and EtOAc. Triturate in acetone to remove insoluable material. Dry, filter, and concentrate. Purify the residue by flash chromatography on silica gel (731 mg, 18%): MS (esi negative) m/z 368.9 (rel intensity) (M−H, 55%), 367.0 (45%).

Workup

  1. temperatureCool
  2. customTriturate in acetone
  3. customto remove insoluable material
  4. customDry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by flash chromatography on silica gel (731 mg, 18%)

Sources & evidence

ORD record
ord-c20574c673c44649b180ccf452108c05
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Linked notes

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