Phenylboronic Acid → HCID 86587854, compound

HRID 393140Notes

Reaction equation

HRID 393140 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:28]2[C:19](=[CH:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[CH:27]=2)[CH:18]=[C:17]2[C:12]=1[C:13]1[CH:44]=[CH:43][C:42]3[C:29](=[CH:30][C:31]4[C:40]([CH:41]=3)=[CH:39][C:38]3[C:33](=[CH:34][C:35](Br)=[CH:36][CH:37]=3)[CH:32]=4)[C:14]=1[CH:15]=[CH:16]2>C1(C)C(C)=CC=CC=1>[C:1]1([C:11]2[C:28]3[C:19](=[CH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[CH:27]=3)[CH:18]=[C:17]3[C:12]=2[C:13]2[CH:44]=[CH:43][C:42]4[C:29](=[CH:30][C:31]5[C:40]([CH:41]=4)=[CH:39][C:38]4[C:33](=[CH:34][C:35]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)=[CH:36][CH:37]=4)[CH:32]=5)[C:14]=2[CH:15]=[CH:16]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 86587855HCID 86587855, compound

Product 1

HCID 86587854HCID 86587854, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Naphthacenonaphthacene (Chemical Abstract Service (CAS) Registry Number 180-50-1) is dissolved in carbon tetrachloride. While the resultant mixture is cooled, 1 mol equivalent of bromine is added thereto. The mixture is reacted for 4 hours and brominated. Thereafter, the mixture is purified in accordance with a usual method, and 6,13-dibromonaphthacenonaphthacene is obtained. 2 mol equivalent of phenylboronic acid [Ph—B(OH)2] (where “Ph” represents a phenyl group) is refluxed and reacted for 12 hours with the 6,13-dibromonaphthacenonaphthacene obtained in this way, in a xylene/2M sodium carbonate aqueous solution, by using 0.01 mol equivalent of tetraquis(triphenylphosphine)palladium (0) [Pd(PPh3)4] (where “Ph” represents a phenyl group) as a catalyst. Thereafter, the resultant mixture is purified in accordance with a usual method, and the 6,13-diphenyl-naphthacenonaphthacene expressed by the following formula is synthesized. (Note that, in the formula, “Ph” represents a phenyl group.)

Workup

  1. temperatureis refluxed
  2. customThereafter, the resultant mixture is purified in accordance with a usual method
  3. customis synthesized

Sources & evidence

ORD record
ord-4e464879107e4ad99fe3c942b0ae62bd
Source dataset
uspto-grants-2004_10
Patent number
US06805977B2

Reaction notes

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