Toluene → Diethyl 2-(2',5'dimethylphenyl)terephthalate

HRID 430880노트

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HRID 430880 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.[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1B(O)O>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>[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[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]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 2734347(2,5-Dimethylphenyl)boronic acidHCID 11033938Diethyl 2-bromoterephthalate

생성물 1

HCID 18676609Diethyl 2-(2',5'dimethylphenyl)terephthalate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
85 °C

실험 절차

Diethyl bromoterephthalate (46.2 g, 150 mmol), K2CO3 (41.5 g, 300 mmol), 140 ml of toluene and 140 ml of H2O were placed in a reaction vessel and argon was passed in for 30 minutes. 2,5-dimethylbenzeneboronic acid (24.8 9, 165 mmol) (cf. B3) and Pd(PPh3)4 (0.7 g, 0.6 mmol) were subsequently added under protective gas. The brownish mixture, which was turbid due to phase separation, was stirred vigorously under a blanket of protective gas at an internal temperature of 85° C. The reaction was complete after 24 hours (according to TLC). 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 yellow oil in sufficient purity (greater than 97%). Yield: 48.7 g (99%).

후처리

  1. customwas passed in for 30 minutes
  2. customdue to phase separation
  3. customAfter phase separation
  4. stirringthe organic phase was shaken with dilute HCl/H2O (until neutral)
  5. stirringThe aqueous phase was shaken with toluene
  6. filtrationAfter filtering off any palladium residues
  7. customthe solution was evaporated
  8. customThe product was obtained as a yellow oil in sufficient purity (greater than 97%)

출처 및 근거

ORD 기록
ord-ec99b08b917d44d69e18b8be22cbc0cf
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323373B1

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