Water → 2-Bromo-7-methylnaphthalene

HRID 2105743Notes

Reaction equation

HRID 2105743 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Br:12])=[CH:7][CH:8]=2)[CH:3]=1.[Li][CH2:14]CCC.CI.O>CCOCC>[Br:12][C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2]([CH3:14])=[CH:11][CH:10]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 6253552,7-DibromonaphthaleneHCID 178418339Butyllithium

Product 1

HCID 153213362-Bromo-7-methylnaphthalene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

Suspension of 2,7-dibromonaphthalene (61.4 g, 0.21 mole) in ether (400 ml) was cooled to −30° C., and n-BuLi (1.6M in hexane, 135 ml, 0.21 mole) was added. Reaction mixture was allowed to warm to room temperature, stirred for additional 2.5 h, cooled to −30° C., and CH3I (13.5 ml, 0.21 mole) was added. Reaction mixture was allowed to warm to room temperature, stirred for additional 16 h, treated by water (100 ml). Organic layer was separated, water layer was extracted by ether (6×100 ml). Combined organic fraction was evaporated, giving practically pure solid product. The yield 38.1 g (82%).

Workup

  1. customReaction mixture
  2. temperatureto warm to room temperature
  3. temperaturecooled to −30° C.
  4. customReaction mixture
  5. temperatureto warm to room temperature
  6. stirringstirred for additional 16 h
  7. customOrganic layer was separated
  8. extractionwater layer was extracted by ether (6×100 ml)
  9. customCombined organic fraction was evaporated
  10. customgiving practically pure solid product

Sources & evidence

ORD record
ord-c12bf8f98e7244df944c14f575aac230
Source dataset
uspto-grants-2009_08
Patent number
US07579417B2

Reaction notes

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