Water → HCID 68800602, compound

HRID 1434496Notes

Reaction equation

HRID 1434496 reaction equation
[CH2:1]([C:7]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:19]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:27][C:28]1[C:29](=O)[C:30]2[C:38](=[CH:39][CH:40]=1)[C:37]1[C:32](=[CH:33][C:34]([Br:41])=[CH:35][CH:36]=1)[CH:31]=2.[OH2:43]>C1COCC1>[CH2:21]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]([C:31]3([OH:43])[C:30]4[CH:29]=[C:28]([Br:27])[CH:40]=[CH:39][C:38]=4[C:37]4[C:32]3=[CH:33][C:34]([Br:41])=[CH:35][CH:36]=4)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 186746002-Bromo-9,9-dihexyl fluoreneHCID 534201032,7Dibromofluorenone

Product 1

HCID 68800602HCID 68800602, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5.64 g of Mg placed into a 1000 ml three-neck flask, 80 g of 9,9-dihexyl-2-bromofluorene in 300 ml THF was slowly added dropwise, to prepare a Grignard reagent. After a temperature of a reaction chamber was decreased to −40° C. or less, 52 g of 2,7-dibromofluorenone was added to the reaction bath in a nitrogen atmosphere. The temperature was gradually increased to room temperature, followed by stirring for 10 hours. The resulting reaction solution was poured into water, after which an extraction was performed using diethyl ether. The solvent was evaporated using a rotary evaporator. A column chromatography separation resulted in 60 g (58%) of (9-(9,9-dihexylfluoren-2-yl)-2,7-dibromofluoren-9-ol) (1).

Workup

  1. customwas decreased to −40° C. or less
  2. customThe resulting reaction solution
  3. extractionafter which an extraction
  4. customThe solvent was evaporated
  5. customa rotary evaporator
  6. customA column chromatography separation
  7. customresulted in 60 g (58%) of (9-(9,9-dihexylfluoren-2-yl)-2,7-dibromofluoren-9-ol) (1)

Sources & evidence

ORD record
ord-990f80f0a1134d03a4f209e688249faa
Source dataset
uspto-grants-2009_11
Patent number
US07615289B2

Reaction notes

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