Boron tribromide → HCID 58473601, compound

HRID 870117Notes

Reaction equation

HRID 870117 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:27][C:28]3[CH:33]=[C:32]([O:34]C)[CH:31]=[C:30]([O:36]C)[CH:29]=3)([CH2:16][C:17]3[CH:22]=[C:21]([O:23]C)[CH:20]=[C:19]([O:25]C)[CH:18]=3)[C:4]=2[CH:3]=1.B(Br)(Br)Br>>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:27][C:28]3[CH:29]=[C:30]([OH:36])[CH:31]=[C:32]([OH:34])[CH:33]=3)([CH2:16][C:17]3[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([OH:25])[CH:18]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 58473530HCID 58473530, compound

Product 1

HCID 58473601HCID 58473601, compoundYield 68%

Procedure

2,7-dibromo-9,9-bis(3,5-dimethoxybenzyl)-9H-fluorene (1.3 g, 2.08 mmol) was added to a round bottom flask charged with a stirbar and equipped with a rubber septum. The flask is purged with nitrogen for 10 min. Anhydrous dichloromethane (20 mL) is transferred to the flask via cannula and the mixture is stirred until the solids are completely dissolved. The solution is then cooled with a dry ice/acetone bath for 10 minutes. BBr3 (6.1 mL, 63.3 mmol) is added dropwise via cannula with constant stirring. The bath is allowed to warm to room temperature and the mixture is stirred overnight. The reaction is quenched with the slow addition of 125 mL of water. The solution is then extracted with 3 portions of ethyl acetate (50 mL). The organic layer is dried over MgSO3, filtered, and dried onto silica. Flash chromatography of the crude using ethyl acetate in dichloromethane gives an off-white crystalline solid (800 mg, 68% yield).

Workup

  1. additioncharged with a stirbar
  2. customequipped with a rubber septum
  3. customThe flask is purged with nitrogen for 10 min
  4. dissolutionare completely dissolved
  5. temperatureThe solution is then cooled with a dry ice/acetone bath for 10 minutes
  6. stirringthe mixture is stirred overnight
  7. customThe reaction is quenched with the slow addition of 125 mL of water
  8. extractionThe solution is then extracted with 3 portions of ethyl acetate (50 mL)
  9. dry with materialThe organic layer is dried over MgSO3
  10. filtrationfiltered
  11. customdried onto silica

Sources & evidence

ORD record
ord-76ff446c011641f5a56977202de26b61
Source dataset
uspto-grants-2015_03
Patent number
US08969509B2

Reaction notes

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