Trimethyl borate → 7-Borono12,12-dimethyl-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene

HRID 634551Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:21]([CH3:29])([CH3:28])[C:22]4[C:27]([C:7]3=[CH:6][C:5]2=1)=[CH:26][CH:25]=[CH:24][CH:23]=4.[Li]CCCC.[B:35](OC)([O:38]C)[O:36]C>C1COCC1>[B:35]([C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:21]([CH3:29])([CH3:28])[C:22]4[C:27]([C:7]3=[CH:6][C:5]2=1)=[CH:26][CH:25]=[CH:24][CH:23]=4)([OH:38])[OH:36]

Participants

Conditions

Temperature: -78 °C

Procedure

22.3 g (51 mmol) of 7-bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene 12 are dissolved in 600 ml of dry THF and cooled to −78° C. At this temperature, 26.2 ml (65.7 mmol/2.5 M in hexane) of n-BuLi are added over the course of about 5 min., and the mixture is subsequently stirred at −78° C. for a further 2.5 h. At this temperature, 7.3 ml (65.7 mmol) of trimethyl borate are added as rapidly as possible, and the reaction is allowed to come slowly to RT (about 18 h). The reaction solution is washed with water, and the precipitated solid and the organic phase are dried azeotropically with toluene. The crude product is washed by stir-ring with toluene/methylene chloride at about 40° C. and filtered off with suction, giving 16 g (82%) of the product as white solid.

Workup

customto come slowly to RT
custom(about 18 h)
washThe reaction solution is washed with water
dry with materialthe precipitated solid and the organic phase are dried azeotropically with toluene
washThe crude product is washed
stirringby stir-ring with toluene/methylene chloride at about 40° C.
filtrationfiltered off with suction

Sources & evidence

ORD record: ord-7bdbaf7d7a7847078fcf5b16aa8daaeb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09324954B2

Reaction notes

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