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

HRID 1818611Notes

Reaction equation

HRID 1818611 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 insoluble 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 insoluble 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-bc2da1bba7c947bb9cdd88ef67e4e1eb
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

Loading…