Bromine → 9-Bromo-10-(4-methylnaphthalen-1-YL)anthracene

HRID 1190233Notes

Reaction equation

HRID 1190233 reaction equation
[Br:1]Br.[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:15]3[C:20]([CH:21]=[C:22]4[C:27]=2[CH:26]=[CH:25][CH:24]=[CH:23]4)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:6][CH:5]=1>ClCCl.C(O)C>[Br:1][C:21]1[C:22]2[C:27]([C:14]([C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:4]([CH3:3])=[CH:5][CH:6]=3)=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 577025649-(4-Methylnaphth-1-yl)anthracene

Product 1

HCID 597583959-Bromo-10-(4-methylnaphthalen-1-YL)anthracene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 18.0 ml (352 mmol) of bromine in 100 ml of dichloromethane is added dropwise with vigorous stirring to a solution of 102.0 g (320 mmol) of 9-(4-methylnaphth-1-yl)anthracene in 2000 ml of dichloromethane at −5° C., and the mixture is stirred at room temperature for 12 h. The suspension is subsequently diluted with 1000 ml of ethanol. The precipitated solid is filtered off with suction, washed with 500 ml of a mixture of water and ethanol (1:1, v:v) and three times with 200 ml of ethanol. After washing twice with 1000 ml of boiling ethanol each time, the solid is dried under reduced pressure. Yield: 108.0 g (84.9% of theory), about 97% according to 1H-NMR.

Workup

  1. additionis added dropwise
  2. filtrationThe precipitated solid is filtered off with suction
  3. washwashed with 500 ml of a mixture of water and ethanol (1:1, v:v) and three times with 200 ml of ethanol
  4. washAfter washing twice with 1000 ml of boiling ethanol each time
  5. customthe solid is dried under reduced pressure

Sources & evidence

ORD record
ord-c651787d16ab4d3ca8ff799b83a841f2
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Reaction notes

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