Toluene → HCID 68337205, compound

HRID 1529515Notes

Reaction equation

HRID 1529515 reaction equation
Cl[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:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:46][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 54371635HCID 54371635, compound

Product 1

HCID 68337205HCID 68337205, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

40 g (115 mmol) of diethyl chloroterephthalate, 19.7 g (162 mmol) of benzeneboronic acid, 389 mg (1.73 mmol) of Pd(OAc)2, 3.36 ml (3.4 mmol) of 1 M tri-tert-butylphosphine in toluene and 75 g (231 mmol) of Cs2 CO3 are heated at the boil for 4 h in 300 ml of 1,4-dioxane. The mixture is subsequently partitioned between toluene and water, and the org. phase is washed three times with water, dried over Na2SO4 and evaporated in a rotary evaporator. The yield is 47 g (115 mmol, 99%).

Workup

  1. customThe mixture is subsequently partitioned between toluene and water
  2. washphase is washed three times with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-c23360bd107c438fa4cf3c5398932ed7
Source dataset
uspto-grants-2015_07
Patent number
US09090590B2

Reaction notes

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