Toluene → HCID 86727954, compound

HRID 628811Notes

Reaction equation

HRID 628811 reaction equation
[C:1]1([PH+:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC[C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:29]([C:36]2[CH:41]=[CH:40][C:39](CBr)=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1.[C:50]1([P:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C1(C)C=CC=CC=1>CN(C=O)C>[C:25]1([C:28]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[C:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:24]=[CH:23][CH:22]=[CH:27][CH:26]=1.[C:14]1([PH+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:63]1([PH+:56]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5241824TriphenylphosphoniumHCID 66591315HCID 66591315, compound

Product 1

HCID 86727954HCID 86727954, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triphenylphosphonium salt, TPE-TPP, was prepared from 3 (0.5 g, 1.0 mmol) and triphenylphosphine (1.0 g, 4.0 mmol) in DMF at 100° C. After stirring for 24 h, the solution was poured into large amount of toluene. The white precipitate was collected in 80% yield. 1H NMR (400 MHz, DMSO-d6), δ (TMS, ppm): 7.90-7.55 (m, 30H), 7.16-6.66 (m, 18H), 5.039 (d, 4H). 13C NMR (100 MHz, DMSO-d6), δ (TMS, ppm): 143.4, 142.5 140.1, 135.2, 134.0, 131.1, 130.6, 130.3, 130.1, 128.0, 127.0, 126.1, 118.1, 17.2, 40.21. m/z (MALDI-TOF) 882.49 [M−2Br)+]; calc. 882.35. Anal. Calcd. C64H52Br2P2: C, 73.7; H, 5.0. Found: C, 73.7; H, 4.9.

Workup

  1. customThe white precipitate was collected in 80% yield

Sources & evidence

ORD record
ord-15a9d54a42734719ab49758f8f6b67b2
Source dataset
uspto-grants-2016_04
Patent number
US09315465B2

Reaction notes

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