Boron tribromide → 9,9-Diethyl-2,7-bis(4-hydroxybiphenyl-4'-yl)fluorene

HRID 984141Notes

Reaction equation

B(Br)(Br)Br.[CH2:5]([C:7]1([CH2:62][CH3:63])[C:19]2[CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32]CCCCCCCC)=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][C:10]([C:41]1[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][C:50]([O:53]CCCCCCCC)=[CH:49][CH:48]=3)=[CH:43][CH:42]=1)=[CH:11][CH:12]=2)[CH3:6]>C(Cl)Cl>[CH2:62]([C:7]1([CH2:5][CH3:6])[C:8]2[CH:9]=[C:10]([C:41]3[CH:42]=[CH:43][C:44]([C:47]4[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=4)=[CH:45][CH:46]=3)[CH:11]=[CH:12][C:13]=2[C:14]2[C:19]1=[CH:18][C:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)=[CH:22][CH:21]=1)=[CH:16][CH:15]=2)[CH3:63]

Participants

Conditions

Temperature: 0 °C

Procedure

Boron tribromide (99.9%, 1.05 cm3, 0.0111 mol) in DCM (10 ml) was added dropwise to a cooled (0° C.) stirred solution of 9,9-diethyl-2,7-bis(4octyloxybiphenyl-4′-yl)fluorene (2.90 g, 0.0037 mol) in DCM (100 cm3). The reaction mixture was stirred at room temperature overnight, then poured onto an ice/water mixture (50 g) and stirred (30 minutes). The crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and hexane (30:70) as the eluent and recrystallisation from ethanol to yield a white powder (0.83 g, 40%, m.pt. >300° C.).

Workup

stirringstirred (30 minutes)
customThe crude product was purified by column chromatography on silica gel with a mixture of ethyl acetate and hexane (30:70) as the eluent and recrystallisation from ethanol

Sources & evidence

ORD record: ord-07b662c302b146b8bbd7edca220f7ce6
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867243B2

Reaction notes

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