Boron tribromide → HCID 66717073, compound

HRID 1502183Notes

Reaction equation

HRID 1502183 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:14][CH:13]=4)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:25][C:22]1[S:21][C:20]([C:15]2[CH:14]=[CH:13][C:12]3[N:11]([C:26]4[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=4)[C:10]4[C:18]([C:17]=3[CH:16]=2)=[CH:19][C:7]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=4)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66717046HCID 66717046, compound

Product 1

HCID 66717073HCID 66717073, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The obtained 3,6-bis(5-methylthiophen-2-yl)-9-(4-methoxyphenyl)carbazole (3.73 g, 8.0 mmol) was dissolved in methylene chloride (30 mL). 1M Methylene chloride solution of boron tribromide (8 mL) was added dropwise to the resultant solution at −10° C., followed by stirring at room temperature. Next, the resultant mixture was washed with water and dried and the solvent was evaporated, to thereby obtain a gray solid. The obtained solid was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (4/1 by volume), to thereby obtain 3.47 g of 3,6-bis(5-methylthiophen-2-yl)-9-(4-hydroxyphenyl)carbazole.

Workup

  1. washNext, the resultant mixture was washed with water
  2. customdried
  3. customthe solvent was evaporated
  4. customto thereby obtain a gray solid
  5. customThe obtained solid was purified through silica gel column chromatography
  6. additiona solvent mixture of methylene chloride/hexane (4/1 by volume)

Sources & evidence

ORD record
ord-088ff24001aa471b807ca09aed3df63b
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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