Iodoethane → 9-Ethyl-1-methyl-9H-fluorene

HRID 1918430Notes

Reaction equation

HRID 1918430 reaction equation
[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Li][CH2:16][CH2:17]CC.ICC>>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:16][CH3:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 156041-MethylfluoreneHCID 178418339Butyllithium

Product 1

HCID 155843679-Ethyl-1-methyl-9H-fluoreneYield 95.7%

Procedure

The substitution reaction at the 9-position was performed according to the general procedure for the synthesis of 9-substituted fluorenes described above in item IV(i). 1-Methylfluorene (47) (3.01 g, 16.7 mmol) was used instead of fluorene, n-BuLi (8.06 ml, 20 mmol, 2.5 M in hexane), RX=1-iodoethane (3.39 g, 21.7 mmol). 48 was isolated to give a colorless oil (3.33 g, 95%).

Workup

  1. customThe substitution reaction at the 9-position
  2. custom48 was isolated

Sources & evidence

ORD record
ord-32580988152d44ab946da499f9a526d4
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

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