Water → 3-BroMo-9-dibenzothiophen-4-yl-9H-carbazole

HRID 1517003Notes

Reaction equation

[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([N:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:3][CH:2]=1.C1C(=O)N([Br:34])C(=O)C1.O>CN(C=O)C>[Br:34][C:23]1[CH:24]=[CH:25][C:26]2[N:14]([C:4]3[C:5]4[S:6][C:7]5[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=5[C:9]=4[CH:1]=[CH:2][CH:3]=3)[C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

Conditions

Temperature: 0 °C

Procedure

9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole (6 g, 17.17 mmol) was dissolved in 100 mL of DMF. The solution was cooled to 0° C. To the solution was added NBS (3.36 g, 18.89 mmol) in 20 mL of DMF dropwise. After stirring at this temperature for 1 h, HPLC indicated there was very little reaction. The reaction was warmed to room temperature and monitored by HPLC. After 24 h, 500 mL of water was added to the reaction and stirred at room temperature for 2 h. The white precipitate was filtered and washed with water. The solid was dissolved in DCM and washed with water and dried over MgSO4. The residue was used directly for the next step. The product contains 10% of starting material, 80% of desired product and 10% of dibrominated product.

Workup

customreaction
temperatureThe reaction was warmed to room temperature
waitAfter 24 h
stirringstirred at room temperature for 2 h
filtrationThe white precipitate was filtered
washwashed with water
dissolutionThe solid was dissolved in DCM
washwashed with water
dry with materialdried over MgSO4

Sources & evidence

ORD record: ord-158356c059e547739301154a06cd1d6c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227801B2

Reaction notes

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