4-Bromoanisole → HCID 18969647, compound

HRID 863137Notes

Reaction equation

HRID 863137 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.[CH2:21]([O:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38]1[CH:43]=[CH:42][C:41]3[O:44][CH2:45][O:46][C:40]=3[CH:39]=1)=[C:33]([C:47]([O:49][CH3:50])=[O:48])[C:32]2=[O:51])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CCOCC.C1COCC1>[CH2:21]([O:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38]1[CH:43]=[CH:42][C:41]3[O:44][CH2:45][O:46][C:40]=3[CH:39]=1)=[C:33]([C:47]([O:49][CH3:50])=[O:48])[C:32]2([OH:51])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 5462224MagnesiumHCID 18427649HCID 18427649, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 18969647HCID 18969647, compoundYield 110.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To dry magnesium turnings (0.96 g, 40 mmol) under an argon atmosphere was added a solution of 4-bromoanisole (7.48 g, 40 mmol) in 9:1 Et2O/THF (50 ml). The resulting 4-methoxyphenyl magnesium bromide solution was added portionwise to a solution of methyl 5-benzyloxy-1-(3,4-methylenedioxyphenyl)-3-oxoindene-2-carboxylate (8.29 g, 20 mmol) in THF (250 ml) under an argon atmosphere. Upon completion of the addition, the mixture was quenched by the addition of 3M HCl and extracted with EtOAc. The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl. The solvent was removed in vacuo to afford the title compound (11.58 g, 100%), which was used without further purification.

Workup

  1. additionUpon completion of the addition
  2. customthe mixture was quenched by the addition of 3M HCl
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-22ac201b1d204705b31ebeb001ce4310
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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