Toluene → Diethyl 2-(4'-hexyloxyphenyl)terephthalate

HRID 1635755노트

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HRID 1635755 반응식
Br[C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.[CH2:31]([O:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:31]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:2]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:42][CH:43]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 36821484-Hexyloxyphenylboronic AcidHCID 11033938Diethyl 2-bromoterephthalate

생성물 1

HCID 11069361Diethyl 2-(4'-hexyloxyphenyl)terephthalate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
85 °C

실험 절차

Diethyl bromoterephthalate (30.1 g, 100 mmol), K2CO3 (27.6 g, 200 mmol) and 140 ml of toluene and 140 ml of H2O were placed in a reaction vessel and argon was passed in for 30 minutes. 4-hexyloxyphenylboronic acid (26.7 g, 120 mmol) (cf. B1) and Pd(PPh3)4 (1.16 g, 1 mmol) were subsequently added under protective gas. The yellow-green, turbid mixture was stirred vigorously under a blanket of protective gas at an internal temperature of 85° C. After 7 hours, the reaction was complete. After phase separation, the organic phase was shaken with dilute HCl/H2O (until neutral). The aqueous phase was shaken with toluene and the organic phases were combined. After filtering off any palladium residues, the solution was evaporated. The product was obtained as a yellowish brown oil in sufficient purity (about 85%): 44.7 g (1112%).

후처리

  1. customwas passed in for 30 minutes
  2. customAfter phase separation
  3. stirringthe organic phase was shaken with dilute HCl/H2O (until neutral)
  4. stirringThe aqueous phase was shaken with toluene
  5. filtrationAfter filtering off any palladium residues
  6. customthe solution was evaporated
  7. customThe product was obtained as a yellowish brown oil in sufficient purity (about 85%)

출처 및 근거

ORD 기록
ord-66b34cb7630745c3b2444332cd92801d
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509507B2

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