Ethyl Acetate → HCID 68531060, compound

HRID 2108667Notes

Reaction equation

HRID 2108667 reaction equation
C([O:9][C:10]1[CH:15]=[C:14]([Br:16])[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:19]=2)=[C:12]([Br:34])[CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1>[Br:16][C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([Br:34])[C:13]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 68530583HCID 68530583, compound

Product 1

HCID 68531060HCID 68531060, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3,5-dibromo-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy]phenyl benzoate (2.14 gm, 3.75 mmol) in THF 60 mL was added 1 N NaOH 20 mL. The reaction was stirred at r.t overnight, then poured into 120 mL ethyl acetate. The aqueous layer was removed and the organic was washed 2× with aqueous NaHCO3, 1× with 1 N HCl 30 mL. The ethyl acetate was dried over Na2SO4, filtered and concentrated under reduced pressure to give 3,5-dibromo-4-[3′-(4-fluorobenzyl)-4′-methoxyphenoxy]phenol (1.68 gm, 93%); 1H NMR (300 MHz, DMSO-d6): δ 10.27 (s, 1H), 7.20 (m, 2H), 7.05 (m, 4H), 6.87 (d, J=9 Hz, 1H), 6.65 (d, J=3.3 Hz, 1H), 6.46 (dd, J=9, 3 Hz, 1H), 3.84 (s, 2H), 3.71 (s, 3H); TLC conditions: Uniplate silica gel, 250 microns; hexane-ethyl acetate [3:1]; Rf=0.65.

Workup

  1. customThe aqueous layer was removed
  2. washthe organic was washed 2× with aqueous NaHCO3, 1× with 1 N HCl 30 mL
  3. dry with materialThe ethyl acetate was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5dacf3d3f9548c1b424cc1140378f02
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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