Sodium Carbonate → HCID 57194638, compound

HRID 2389328Notes

Reaction equation

HRID 2389328 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[OH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[OH:15][CH2:16][C:17]1[CH:22]=[C:21]([C:2]2[CH:14]=[CH:13][CH:12]=[C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 5197439Ethyl 2-(3-bromophenoxy)acetate

Product 1

HCID 57194638HCID 57194638, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (3-bromophenoxy)acetate (488 mg) in DME (10 mL) was added 3-(hydroxymethyl)phenylboronic acid (429 mg), 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride (77 mg) and 2M Na2CO3 aqueous solution (5 mL) at ambient temperature. The reaction mixture was stirred at 80° C. for 7 hours. The resulting mixture was cooled to ambient temperature and diluted with EtOAc. The mixture was washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3) to give ethyl {[3′-(hydroxymethyl)-3-biphenylyl]oxy}acetate.

Workup

  1. temperatureThe resulting mixture was cooled to ambient temperature
  2. washThe mixture was washed successively with water and brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-97:3)

Sources & evidence

ORD record
ord-390216ad359e4707b2db09b8a13a684a
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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