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Sodium Carbonate → (5-Fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetic acid

HRID 2250885
Notes
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Reaction equation

HRID 2250885 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1Br)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>COCCOC>[F:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:5])=[O:17])=[C:10]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][C:25]([F:24])([F:37])[F:36])[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 59642165Tert-butyl (2-bromo-4-fluorophenoxy)acetate

Product 1

HCID 58689904(5-Fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Procedure

A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid-t-butyl ester (5.1 g, 16.71 mmol) in DME (60 ml)/2M Na2CO3 (29.25 ml, 58.50 mmol) was treated with 2-trifluoromethoxyphenylboronic acid (5.16 g, 25.08 mmol), and Pd[PPh3]4 (3.87 g, 3.33 mmol) in a microwave oven at 150° C. for 15 min. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was successively washed with 1N NaOH and brine, then dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 8-10% ethyl acetate/hexanes gradient to afford 4.65 g of colorless oil (t-butyl ester). This material was dissolved in 4N HCl/dioxane (40 ml) and stirred at 60° C. for 2 h and then at rt overnight. Concentration under reduced pressure afforded the product as colorless oil (4.17 g, 24%).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was successively washed with 1N NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 8-10% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-024b27cfc35b4f7297aa864f31e02fd1
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07317125B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes