BENZ(a)ANTHRACENE → 7-Bromobenzanthracene

HRID 1170771Notes

Reaction equation

HRID 1170771 reaction equation
CN(C=O)C.[CH:6]1[C:23]2[C:22]3[CH:21]=[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=[CH:19]4)=[CH:14][C:13]=3[CH:12]=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.C1C(=O)N([Br:31])C(=O)C1.BrC1CC(=O)NC1=O>O>[Br:31][C:14]1[C:13]2[CH:12]=[CH:11][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:23]=3[C:22]=2[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2

Participants

6

Reactant 4

HCID 5954BENZ(a)ANTHRACENEHCID 6228Dimethylformamide2×HCID 38309BromosuccinimideHCID 67184N-bromobutanimide

Product 1

HCID 728497-BromobenzanthraceneYield 91.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 300 ml of DMF, N,N-dimethylformamide, 40 g of commercial benzanthracene was dispersed, and 35.6 g of NBS, bromosuccinimide, was added to the resultant suspension at the room temperature. After the resultant mixture was stirred for 3.5 hours, 600 ml of water was added, and the formed crystals were separated by filtration and washed with methanol. The obtained crude crystals were purified using a silica gel column with toluene and filtered with hexane, and 49.3 g of 7-bromobenzanthracene was obtained as cream crystals (the yield: 91%).

Workup

  1. customthe formed crystals were separated by filtration
  2. washwashed with methanol
  3. customThe obtained crude crystals
  4. customwere purified
  5. filtrationfiltered with hexane

Sources & evidence

ORD record
ord-76886b2c671141248132ee6e78ef58d3
Source dataset
uspto-grants-2010_11
Patent number
US07829206B2

Reaction notes

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