Bromine → 10-Bromophenanthrene-2-carboxylic acid

HRID 895377Notes

Reaction equation

[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([OH:17])=[O:16].[Br:18]Br>C(O)(=O)C>[Br:18][C:13]1[C:14]2[CH:1]=[C:2]([C:15]([OH:17])=[O:16])[CH:3]=[CH:4][C:5]=2[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Phenanthrene-2-carboxylic acid (1, 0.116 g, 0.5 mmol) was dissolved in acetic acid at 70° C. and then bromine (0.027 ml, 0.5 mmol) was added. The mixture was stirred at 70° C. overnight. The following day, bromine (0.027 ml, 0.5 mmol) was added and the mixture was refluxed for 6 h and then allowed to cool. The resulting precipitate was collected by filtration. 1H NMR (270 MHz, DMSO):—7.8 (m, 2H), 8.1 (d, 1H), 8.25 (d, 1H), 8.45 (s, 1H), 8.9 (s, 1H), 8.95 (m, 1H) and 9.05 (d, 1H).

Workup

temperaturethe mixture was refluxed for 6 h
temperatureto cool
filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-4e18be51a9044745aef627492e4254ac
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916816B2

Reaction notes

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