Water → 2-[4',7'-Diphenylspiro(fluorene-9,2'-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

HRID 1828620Notes

Reaction equation

HRID 1828620 reaction equation
[Li]CCCC.BrC1C=[CH:11][C:10]2[C:13]3[C:18]([C:19]4([CH:27]=[C:26]5[C:21]([C:22]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)=[CH:23][CH:24]=[C:25]5[C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:20]4)[C:9]=2C=1)=[CH:17][CH:16]=[CH:15][CH:14]=3.[CH:40]([B:43]1[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:51])([CH3:50])[O:44]1)([CH3:42])[CH3:41].O>C1COCC1.CCOCC>[C:34]1([C:22]2[C:21]3[C:26]([C:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=2)=[CH:27][C:19]2([C:9]4[CH:42]=[C:40]([B:43]5[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:51])([CH3:50])[O:44]5)[CH:41]=[CH:11][C:10]=4[C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:20]=3)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 962WaterHCID 127277112-Isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 220657992-Bromo-4',7'-diphenylspiro(fluorene-9,2'-indene)HCID 178418339Butyllithium

Product 1

HCID 220657892-[4',7'-Diphenylspiro(fluorene-9,2'-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolaneYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (1.2 equiv) is added to a solution of 2-bromo-4′,7′-diphenylspiro(fluorene-9,2′-indene) (6b) in anhydrous THF at −78° C. After stirring the mixture for 1 h, 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 equiv) is added. The reaction mixture is allowed to warm to room temperature and then is stirred overnight. The reaction mixture is mixed with a large amount of water for extraction with ether. The organic extracts are washed with brine before drying over anhydrous MgSO4. The crude product of 2-[4′,7′-diphenylspiro(fluorene-9,2′-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (7b) is purified by column chromatography on silica gel using methylene chloride as the eluent yielding a white powder (79%).

Workup

  1. stirringis stirred overnight
  2. washThe organic extracts are washed with brine
  3. dry with materialbefore drying over anhydrous MgSO4
  4. customThe crude product of 2-[4′,7′-diphenylspiro(fluorene-9,2′-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (7b) is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-eff38b8381e741e9bba4fa2876cc1b07
Source dataset
uspto-grants-2006_06
Patent number
US07057009B2

Reaction notes

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