Chlorosuccinimide → 5-Chloro-3-dodecyl-2-(trimethylsilyl)ethynylthiophene

HRID 732842

반응식

HRID 732842 반응식
Br[C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(C1C=CSC=1)CCCCCCCCCCC.BrN1C(=O)CCC1=O.BrC1SC=CC=1CCCCCCCCCCCC.ClN1C(=O)CCC1=O.[CH3:71][Si:72]([C:75]#[CH:76])([CH3:74])[CH3:73]>CN(C)C=O.C(N(CC)CC)C.[Cu]I>[Cl:19][C:4]1[S:3][C:2]([C:76]#[C:75][Si:72]([CH3:74])([CH3:73])[CH3:71])=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:5]=1

참가 물질

10

반응물 6

HCID 31398ChlorosuccinimideHCID 66111TrimethylsilylacetyleneHCID 67184N-bromobutanimideHCID 27336553-DodecylthiopheneHCID 104268162-Bromo-3-DodecylthiopheneHCID 577550662-Bromo-5-chloro-3-dodecylthiophene3회

생성물 1

HCID 577550635-Chloro-3-dodecyl-2-(trimethylsilyl)ethynylthiophene

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

First, 2-bromo-5-chloro-3-dodecylthiophene can be prepared by brominating 3-dodecylthiophene with 1 molar equivalent of N-bromosuccinimide (NBS) in N,N-dimethylformamide (DMF) at room temperature (rt) (as used herein, “room temperature” refers, for example, to a temperature ranging from about 22° C. to about 25° C.). Next, the chlorination of 2-bromo-3-dodecylthiophene with 1 molar equivalent of N-chlorosuccinimide (NCS) at room temperature generates 2-bromo-5-chloro-3-dodecylthiophene. Subsequently, 2-bromo-5-chloro-3-dodecylthiophene is reacted with a trimethylsilylacetylene in the presence of dichlorobis(triphenylphosphine) palladium (II) (Pd(PPh3)2Cl2) and copper (I) iodide (CuI) in triethylamine (Et3N) at elevated temperatures, such as 50° C. for a suitable time like 24 hours, and 80° C. for 3 hours under argon to form 5-chloro-3-dodecyl-2-(trimethylsilyl)ethynylthiophene. 5-Chloro-3-dodecyl-2-(trimethylsilyl)ethynylthiophene is stirred in a mixture of methanol/dichloromethane (1/2, v/v) in the presence of 10 percent mol of potassium carbonate at room temperature for a suitable time like 16 hours to produce 5-chloro-3-dodecyl-2-ethynylthiophene. 5-Chloro-3-dodecyl-2-ethynylthiophene is then reacted with isopropylmagnesium chloride, and then with anthraquinone or 6,13-pentacenequinone at 50° C. in tetrahydrofuran (THF) under argon, followed by reduction with tin (II) chloride (SnCl2) solution in 10 percent HCl at elevated temperatures like 50° C. The resultant 9,10-bis(5-chloro-3-dodecylthienylethynyl)anthracene (M1) or 6,13-bis(5-chloro-3-dodecylthienylethynyl) pentacene (M2) is polymerized using zinc in the presence of nickel (II) chloride (NiCl2), 2,2′-dipyridil, triphenylphosphine (PPh3) in N,N-dimethylacetamide (DMAc) at elevated temperatures like 80° C. for a suitable time like 48 hours. Poly(9,10-bis(3-dodecylthienylethynyl)anthracene (6a) and poly(6,13-bis(3-dodecylthienylethynyl) pentacene (22a) are thus obtained.

후처리

  1. customat room temperature
  2. custom(rt)
  3. custom“room temperature”
  4. customranging from about 22° C. to about 25° C.
  5. customat room temperature

출처 및 근거

ORD 기록
ord-ff2ceda49cb74fafbb82c4d0718447eb
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07586120B2

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