4-Bromoanisole → HCID 54186372, compound

HRID 862918Notes

Reaction equation

HRID 862918 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:21]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37](=[O:44])[C:36]=2[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:31][CH:30]=1)[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CCOCC.CCOCC.C1COCC1>[O:21]([C:29]1[CH:30]=[CH:31][C:32]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]([OH:44])([C:3]3[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=3)[C:36]=2[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:33][CH:34]=1)[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 5462224MagnesiumHCID 53752512HCID 53752512, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 54186372HCID 54186372, compoundYield 113.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To dry magnesium turnings (119 mg, 4.9 mmol) under an argon atmosphere was added, portionwise, a solution of p-bromoanisole (0.61 ml, 4.9 mmol) in 9:1 Et2O/THF (10 ml). The resulting p-methoxyphenyl magnesium bromide solution was added to a solution of ethyl 3-(4-t-butyldimethylsiloxyphenyl)-1-oxoindene-2-carboxylate (1.00 g, 2.5 mmol) in Et2O (60 ml) under an argon atmosphere at 0° C. The resulting mixture was allowed to warm to room temperature and was stirred for 5 min. The mixture was partitioned between 3M HCl and EtOAc. The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to provide the title compound (1.47 g) which was used without further purification.

Workup

  1. customThe mixture was partitioned between 3M HCl and EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  4. customdried
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8464cf4529034566851cb2a9300dd9c3
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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