Hydrochloric Acid → HCID 86730009, compound

HRID 1753714Notes

Reaction equation

[Li]CCCC.CCCCCC.Br[C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19]3[CH:21]=[CH:22][C:23]([N:25]4[C:37]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:31]5[C:26]4=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:24][C:18]=3[C:17]=2[CH:38]=1.C[O:40][B:41](OC)[O:42]C.Cl>O1CCCC1>[CH:36]1[C:37]2[N:25]([C:23]3[CH:22]=[CH:21][C:19]4[S:20][C:16]5[CH:15]=[CH:14][C:13]([B:41]([OH:42])[OH:40])=[CH:38][C:17]=5[C:18]=4[CH:24]=3)[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]=2[CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

An excess of 1.6M n-BuLi in hexane (30 mL, 48 mmol) was added to a solution of 9-(8-bromodibenzo[b,d]thiophen-2-yl)-9H-carbazole (18.6 g, 43.4 mmol) in 500 ml dry tetrahydrofuran at −78° C. under N2. The reaction mixture was then maintained at 0° C. for 1 h before cooling to −78° C. Trimethylborate (5.9 g, 56 mmol) was added dropwise, the solution was then warmed slowly to room temperature and stirred for 24 h. 2N HCl (100 ml) was added and then the mixture was stirred for a further 1 h. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum, and the residue was crystallized from n-hexane to give 8-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-2-ylboronic acid 11.9 g (63%).

Workup

temperaturebefore cooling to −78° C
temperaturethe solution was then warmed slowly to room temperature
stirringthe mixture was stirred for a further 1 h
extractionThe reaction mixture was extracted with ethyl acetate and water
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was evaporated in vacuum
customthe residue was crystallized from n-hexane

Sources & evidence

ORD record: ord-5a0316283bb14a79a9c5cb5a3d372905
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09166177B2

Reaction notes

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