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4-Bromoanisole → 1-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 650388
Notes
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Reaction equation

HRID 650388 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.COC1C=CC([Mg]Br)=CC=1.O=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:23]1[C:37]([O:39]CC)=[O:38]>C1COCC1.CCOCC.CCOCC>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:23]2[C:37]([OH:39])=[O:38])=[CH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 5462224MagnesiumHCID 18427658Ethyl 1-oxo-3-phenylindene-2-carboxylateHCID 178491912HCID 178491912, compound

Product 1

HCID 159084991-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 21868444Ether tetrahydrofuranSolvent

Procedure

Ethyl (1RS)[1-Hydroxy-1-(4methoxyphenyl)1-3-phenylindene-2-carboxylate. To dry magnesium turnings (0.88 g, 36 mmol) under an argon atmosphere was added, portionwise, a solution of p-bromoanisole (4.5 ml, 36 mmol) in 5% THF/Et2O (37 ml). The resulting p-methoxyphenyl magnesium bromide solution was added to a solution of ethyl 1-oxo-3-phenylindene-2-carboxylate (5.0 g, 18 mmol) in Et2O (300 ml) under an argon atmosphere at 0° C. The resulting mixture was allowed to warm to room temperature and was stirred for 10 min. The mixture was partitioned between 3M HCl (100 ml) and EtOAc (200 ml). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent was removed in vacuo to provide a yellow oil which was treated with Et2O/hexanes. The solid which formed was collected by filtration (3.47 g). The filtrate was concentrated under reduced pressure and purified by flash chromatography. The material which was isolated was treated with Et2O/ hexanes, and the additional solid which formed (1.76 g, 75% total yield) was collected by filtration to afford the title compound.

Workup

  1. customThe mixture was partitioned between 3M HCl (100 ml) and EtOAc (200 ml)
  2. extractionThe organic extract
  3. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customto provide a yellow oil which
  7. customThe solid which formed
  8. filtrationwas collected by filtration (3.47 g)
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. custompurified by flash chromatography
  11. customThe material which was isolated
  12. customthe additional solid which formed
  13. custom(1.76 g, 75% total yield)
  14. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-78c43590651c4c699039c8981617f620
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06271399B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes