2-Bromoanisole → HCID 178506687, compound

HRID 1893142Notes

Reaction equation

HRID 1893142 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li:14])CCC>CCCCC.CCCCCC>[Li:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

5

Reactant 2

HCID 113582-BromoanisoleHCID 178418339Butyllithium

Product 1

HCID 178506687HCID 178506687, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8058HexaneSolvent

Procedure

2-Bromoanisole (97.0 g, 0.52 mol, 1.0 eq) was dissolved in 150 ml pentane. A 1.6M solution of n-butyllithium (0.52 mol, 1.0 eq) in 325 ml hexane was slowly added drop wise with vigorous stirring and cooling with an ice bath. A white suspension formed which was stirred for a further 3 hours at 0° C., then for 9 hours at room temperature. The white solid was filtered off and washed with pentane (4×30 ml). After drying under vacuum, 2-lithioanisole was isolated as a fine white powder.

Workup

  1. temperaturecooling with an ice bath
  2. customA white suspension formed which
  3. stirringwas stirred for a further 3 hours at 0° C.
  4. filtrationThe white solid was filtered off
  5. washwashed with pentane (4×30 ml)
  6. customAfter drying under vacuum

Sources & evidence

ORD record
ord-e55d254c2d58440dbf8948708e5a856c
Source dataset
uspto-grants-2013_08
Patent number
US08513177B2

Reaction notes

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