(+-)-Acenaphthenol → 5-Bromo-1-acenaphthenol

HRID 2056734Notes

Reaction equation

HRID 2056734 reaction equation
[CH:1]1([OH:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C>[Br:14][C:6]1[C:7]2[C:12]3[C:3]([CH2:2][CH:1]([OH:13])[C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 22750(+-)-AcenaphthenolHCID 67184N-bromobutanimide

Product 1

HCID 687021195-Bromo-1-acenaphthenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1,2-dihydro-1-acenaphthylenol (0.34 g, 2 mmol) in dry DMF (10 mL) was added recrystallised N-bromosuccinimide (0.39 g, 2.2 mmol), and the mixture stirred for 3 h under nitrogen. The solution was poured onto water (500 mL) and the precipitate filtered off. The resultant solid was redissolved in methanol, filtered and evaporated in vacuo to yield the title compound as a brown solid.

Workup

  1. additionThe solution was poured onto water (500 mL)
  2. filtrationthe precipitate filtered off
  3. dissolutionThe resultant solid was redissolved in methanol
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd292a748557485e9c647d1c732499b7
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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