Imidazole → 11-Bromomethyl-9,10-dihydro-9,10-ethanoanthracene

HRID 1613225Notes

Reaction equation

HRID 1613225 reaction equation
[CH:1]1[C:14]2[CH:13]3[CH2:15][CH:16]([CH2:17]O)[CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.ClP(C1C=CC=CC=1)C1C=CC=CC=1.[Br:38]Br>C1(C)C=CC=CC=1>[Br:38][CH2:17][CH:16]1[CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=3[CH:13]([C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:15]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24408BromineHCID 66180ChlorodiphenylphosphineHCID 2443799,10-Dihydro-9,10-ethanoanthracene-11-methanol

Product 1

HCID 352223811-Bromomethyl-9,10-dihydro-9,10-ethanoanthracene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9,10-Dihydro-9,10-ethanoanthracene-11-methanol (1.2 gm), imidazole (0.7 gm) and chlorodiphenylphosphine (1.4 gm) were combined in toluene (80 ml) and treated dropwise with bromine (1.0 gm). The mixture was stirred 10 minutes, then extracted with 10% sodium hydroxide (50 ml) and water (50 ml). The toluene was removed on a rotary evaporator and the residue was dissolved in 1:1 methylene chloride/hexane and placed on a silica gel column. The column was eluted with 1:1 methylene chloride/hexane and the eluant removed on a rotary evaporator to give the product.

Workup

  1. extractionextracted with 10% sodium hydroxide (50 ml) and water (50 ml)
  2. customThe toluene was removed on a rotary evaporator
  3. dissolutionthe residue was dissolved in 1:1 methylene chloride/hexane
  4. washThe column was eluted with 1:1 methylene chloride/hexane
  5. customthe eluant removed on a rotary evaporator
  6. customto give the product

Sources & evidence

ORD record
ord-09b3a976ab4542a1a7d4dc0b7acc113b
Source dataset
uspto-grants-1993_03
Patent number
US05192762

Reaction notes

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