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

HRID 990173
ノート
印刷プレビュー

反応式

HRID 990173 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

Diethyl bromoterephthalate (45.2 g, 150 mmol), K2CO3 (41.5 g, 300 mmol), 140 ml of toluene and 140 ml of H2O were placed in the reaction vessel and flushed with argon for 30 minutes. 2,5-Dimethylbenzeneboronic acid (24.8 g, 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 as a result of 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 satisfactory purity (greater than 97%). Yield: 48.7 g (99%).

後処理

  1. customflushed with argon for 30 minutes
  2. customa result of 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 satisfactory purity (greater than 97%)

出典と根拠

ORDレコード
ord-44e3162f61cf41b6bd42c16bff9655f4
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06458909B1

反応ノート

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