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Bromine → 4-[4-(4,4'-Dipentylbicyclohexyl-4-ylethynyl)-2-fluorophenylethynyl]-4,4'-dipentylbicyclohexyl

HRID 1532539
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HRID 1532539 반응식
BrC1C=C[C:5]([C:8]#[C:9][C:10]2([CH2:27]CCCC)[CH2:15][CH2:14][CH:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[C:4](F)[CH:3]=1.C(C1(C=O)CCC(C2CCC(CCCCC)CC2)CC1)CCCC.[Br-].Br[C:59]1[CH:84]=[CH:83][C:62]([CH2:63][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:61]([F:85])[CH:60]=1.BrBr.[C:88]([C:90]1([CH2:107][CH2:108][CH2:109][CH2:110][CH3:111])[CH2:95][CH2:94][CH:93]([CH:96]2[CH2:101][CH2:100][CH:99]([CH2:102][CH2:103][CH2:104][CH2:105][CH3:106])[CH2:98][CH2:97]2)[CH2:92][CH2:91]1)#[CH:89]>N1CCCC1>[CH2:107]([C:90]1([C:88]#[C:89][C:59]2[CH:84]=[CH:83][C:62]([C:63]#[C:27][C:10]3([CH2:9][CH2:8][CH2:5][CH2:4][CH3:3])[CH2:15][CH2:14][CH:13]([CH:16]4[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]4)[CH2:12][CH2:11]3)=[C:61]([F:85])[CH:60]=2)[CH2:91][CH2:92][CH:93]([CH:96]2[CH2:101][CH2:100][CH:99]([CH2:102][CH2:103][CH2:104][CH2:105][CH3:106])[CH2:98][CH2:97]2)[CH2:94][CH2:95]1)[CH2:108][CH2:109][CH2:110][CH3:111]
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반응물 5

HCID 24408BromineHCID 11114149(4-Bromo-2-fluorobenzyl)triphenylphosphonium bromideHCID 154519764-Ethynyl-4,4'-dipentylbicyclohexylHCID 154568234,4'-Dipentylbicyclohexyl-4-carbaldehydeHCID 220133884-(4-Bromo-2-fluorophenylethynyl)-4,4'-dipentylbicyclohexyl

생성물 1

HCID 22013393
4-[4-(4,4'-Dipentylbicyclohexyl-4-ylethynyl)-2-fluorophenylethynyl]-4,4'-dipentylbicyclohexyl

시약·촉매·용매 1

HCID 31268Pyrrolidine용매

실험 절차

0.908 g of 4-(4-bromo-2-fluorophenylethynyl)-4,4′-dipentylbicyclohexyl (obtainable by Wittig reaction of 4,4′-dipentylbicyclohexyl-4-carbaldehyde with 4-bromo-2-fluorobenzyltriphenylphosphonium bromide, addition of bromine onto the resultant alkene and subsequent dehydrobromination using a base), 0.715 g of 4-ethynyl-4,4′-dipentylbicyclohexyl and 0.104 g of tetrakis-(triphenylphosphine)palladium(0) are stirred overnight at 80° C. in 5 ml of pyrrolidine. Conventional work-up gives 4-[4-(4,4′-dipentylbicyclohexyl-4-ylethynyl)-2-fluorophenylethynyl]-4,4′-dipentylbicyclohexyl (C 177 I).

출처 및 근거

ORD 기록
ord-3f03c3bdfddc4a668b637aab4aa98474
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06203724B1

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