Hydrochloric Acid → HCID 68001586, compound

HRID 571591Notes

Reaction equation

HRID 571591 reaction equation
Br[C:2]1[C:7]2=[CH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:10]3[C:20]([C:19]4=[C:21]5[C:11]3=[CH:12][CH:13]=[CH:14][C:15]5=[CH:16][CH:17]=[CH:18]4)=[C:6]2[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:4][CH:3]=1.C([Li])CCC.[B:39]([O:46]CC)([O:43]CC)OCC.Cl>C1COCC1.CCCCCC>[C:22]1([C:9]2[CH:8]=[C:7]3[C:2]([B:39]([OH:43])[OH:46])=[CH:3][CH:4]=[C:5]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:6]3=[C:20]3[C:10]=2[C:11]2[C:21]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]3=4)[CH:14]=[CH:13][CH:12]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 68001497HCID 68001497, compoundHCID 178418339Butyllithium

Product 1

HCID 68001586HCID 68001586, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-80 °C

Procedure

An amount of 3 g (6.21 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1 was dissolved in dehydrated THF and cooled to −80° C. Then, 4.3 ml (6.8 mmol) of a solution of n butyllithium in n-hexane was added dropwise. Forty minutes later, 1.81 g (12.4 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was passed and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 1.51 g (3.37 mmol) of 7,12-diphenylbenzofluoranthene-9-boronic acid. The yield was 54.3%.

Workup

  1. customAfter two-hour reaction
  2. customThen, the separated organic layer was recrystallized

Sources & evidence

ORD record
ord-fe906e1804484c12b5e74305de68f169
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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