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

HRID 990172Notes

Reaction equation

HRID 990172 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.[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Diethyl bromoterephthalate (30.1 g, 100 mmol), K2CO3 (27.6 g, 200 mmol), 140 ml of toluene and 140 ml of H2O were placed in the reaction vessel and flushed with argon 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 yellowish 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 filtration from any palladium residues, the solution was evaporated.

Workup

  1. customflushed with argon 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 filtration from any palladium residues
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-692bb8ce78f145eab6efe8ebd25d2af2
Source dataset
uspto-grants-2002_10
Patent number
US06458909B1

Reaction notes

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