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

HRID 1635756ノート

反応式

HRID 1635756 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

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 178418397HCID 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 a reaction vessel and argon was passed in for 30 minutes. 2,5-dimethylbenzeneboronic acid (24.8 g, 165 mmol) (cf. B3) and Pd(PPh3)4 (0.7g, 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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-28ba6502807c4369be23e9c5a248a42f
出典データセット
uspto-grants-2003_01
特許番号
US06509507B2

反応ノート

読み込み中…