2-Bromo-1-(2-bromoethoxy)-4-methylbenzene → 5-Methyl-2,3-dihydro-1-benzofuran

HRID 1500460Notes

Reaction equation

HRID 1500460 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH2:11]Br.[Li]CCCC>C1COCC1>[CH3:8][C:6]1[CH:7]=[CH:2][C:3]2[O:9][CH2:10][CH2:11][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 110337092-Bromo-1-(2-bromoethoxy)-4-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 127251905-Methyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromo-1-(2-bromoethoxy)-4-methylbenzene (1a) (1.0 g, 3.4 mmol) in THF (20 mL) at −78° C., under N2 was added n-BuLi (2.5 M, 11 mL, 27 mmol) and the resulting mixture was stirred at −78° C., for 1 h. The mixture was quenched with saturated NH4Cl (10 mL), extracted with EtOAc (150 mL), washed with brine, dried and concentrated to give the title compound (1b) as a colorless oil.

Workup

  1. customThe mixture was quenched with saturated NH4Cl (10 mL)
  2. extractionextracted with EtOAc (150 mL)
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4a39f46beea4c1f884da0aef3ad7b80
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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