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

HRID 990173Notes

Reaction equation

HRID 990173 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-44e3162f61cf41b6bd42c16bff9655f4
Source dataset
uspto-grants-2002_10
Patent number
US06458909B1

Reaction notes

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