Bromine → 2-Bromo-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532588Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH2:14][C:15]4[S:16][CH:17]=[CH:18][C:19]=4[C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1.[Br:20]Br>C(O)(=O)C>[Br:20][C:17]1[S:16][C:15]2[CH2:14][C:13]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[N:10][NH:11][C:12]=3[C:19]=2[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-(4-Methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.13 g, 0.5 mmol) was added with a solution of bromine in glacial acetic acid (0.5 mL of a 3 M solution). The reaction mixture was heated at 80° C. for 12 hr. The solution was cooled to room temperature and poured into ice water. The resultant precipitate was filtered, washed with water to provide the corresponding 2-Bromo-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.16 g, 0.46 mmol) as yellow solid in 91% yield.

Workup

temperatureThe solution was cooled to room temperature
filtrationThe resultant precipitate was filtered
washwashed with water

Sources & evidence

ORD record: ord-01f709228a764a228c5d1c43740d87d6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

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