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

HRID 1161094

Reaction equation

HRID 1161094 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[Br:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:8][C:7]2[CH:6]=[CH:5][C:4]([C:9](=[O:11])[CH3:10])=[C:3]([OH:12])[C:2]=2[Cl:1])=[CH:17][CH:16]=1

Participants

6

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)ethanoneYield 26%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine 1-(3-chloro-2,4-dihydroxy-phenyl)-ethanone (6.00 g, 32.2 mmol) and 1,4-bis-bromomethyl-benzene (8.48 g, 31.2 mmol) and potassium carbonate (4.44 g, 32.2 mmol) in acetone (400 ml) and heat to reflux. After 1 h, cool to room temperature and add 10% hydrochloric acid (300 mL). Filter to collect and triturate resultant solid in 1:1 ether/hexanes. Purify by column chromatography, eluting with 40% tetrahydrofuran/hexanes to obtain 1-[4-(4-bromomethyl-benzyloxy)-3-chloro-2-hydroxy-phenyl]-ethanone (3.00 g, 8.12 mmol) as a white solid. MS (m/z): 368.9 (M−1).

Workup

  1. filtrationFilter
  2. customto collect
  3. customtriturate resultant solid in 1:1 ether/hexanes
  4. customPurify by column chromatography
  5. washeluting with 40% tetrahydrofuran/hexanes

Sources & evidence

ORD record
ord-a08bc461023f4de2965f02973e5f2415
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Linked notes

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