Dimethylformamide → HCID 131734302, compound

HRID 1502192Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[N:5]([C:16]3[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].CN(C)C=[O:38]>>[OH:38][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:4]1[CH:3]=[CH:2][CH:14]=[CH:13][C:12]=1[C:11]1[C:6]2[NH:5][C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 1626071-Octanol, 8-bromo-

HCID 71238581HCID 71238581, compound

Product 1

HCID 131734302HCID 131734302, compound

Procedure

2,7-Dibromo-N-(4-hydroxyphenyl)carbazole (1.24 g) and 60% sodium hydride (0.11 g) were added at 0° C. to N,N-dimethylformamide (DMF) (40 mL), followed by stirring for 1 hour. Then, 8-bromooctanol (0.65 g) was added thereto, and the mixture was stirred at room temperature for 3 hours and at 50° C. for 2 hours. The resultant mixture was extracted with ethyl acetate, washed with water and dried. The crude product was treated through silica gel column chromatography (eluent: 25% ethyl acetate/toluene solution), to thereby obtain 1.30 g of 2,7-dibromo-N-4-[(8-hydroxyoctyloxyphenyl]carbazole as colorless viscous liquid.

Workup

stirringthe mixture was stirred at room temperature for 3 hours and at 50° C. for 2 hours
extractionThe resultant mixture was extracted with ethyl acetate
washwashed with water
customdried
additionThe crude product was treated through silica gel column chromatography (eluent: 25% ethyl acetate/toluene solution)

Sources & evidence

ORD record: ord-269f1815b1524047979e656e21d2d2aa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206202B2

Reaction notes

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