Benzene, 1-bromo-3,5-dimethyl- → (3,5-dimethylphenyl)(2-methylcyclopropyl)Methanone

HRID 1458369Notes

Reaction equation

HRID 1458369 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:22][CH:21]1[CH3:23])=[O:19]>CCCCCC>[CH3:9][C:4]1[CH:3]=[C:2]([C:18]([CH:20]2[CH2:22][CH:21]2[CH3:23])=[O:19])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

5

Reactant 3

HCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 45084206N-methoxy-N,2-dimethylcyclopropane-1-carboxamideHCID 178418339Butyllithium

Product 1

HCID 21249913(3,5-dimethylphenyl)(2-methylcyclopropyl)Methanone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 5-bromo-meta-xylene (5.7 mL in 120 mL of dry tetrahydrofuran) at -78° C. was added 30.6 mL of a 1.4M solution of n-butyllithium in hexane and the mixture stirred at low temperature. After 15 minutes, a solution of 2-methylcyclopropanecarboxylic acid N-methoxy-N-methyl-amide (5.0 g in 50 mL tetrahydrofuran) was added dropwise over 5 minutes and the mixture then allowed to warm slowly to room temperature. After 1 hour, the reaction was quenched by the addition of 20 mL 2N hydrochloric acid and 40 mL water. This was extracted with ethyl acetate washed with saturated sodium bicarbonate and brine then dried over sodium sulfate to give 6.95 g of the title compound (crude).

Workup

  1. waitAfter 1 hour
  2. customthe reaction was quenched by the addition of 20 mL 2N hydrochloric acid and 40 mL water
  3. extractionThis was extracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialthen dried over sodium sulfate

Sources & evidence

ORD record
ord-f3db78bba5784916a0720c12295021d7
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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