Nitrogen → HCID 17938208, compound

HRID 1182321Notes

Reaction equation

HRID 1182321 reaction equation
[CH3:1][CH:2]([CH2:18][CH3:19])[CH2:3][O:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15].[CH3:20][CH:21]([CH2:39][CH3:40])[CH2:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34].C([O-])([O-])=O.[K+].[K+].N#N.[C-]#N.[Na+]>C1(C)C=CC=CC=1.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>[CH3:1][CH:2]([CH2:18][CH3:19])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:26]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH:32]([CH3:35])[CH2:33][CH3:34])=[C:24]([O:23][CH2:22][CH:21]([CH3:20])[CH2:39][CH3:40])[CH:25]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15]

Participants

9

Reactant 5

HCID 947NitrogenHCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 22146233[3,4-Bis(2-methylbutoxy)phenyl]boronic acidHCID 22146252HCID 22146252, compound

Product 1

HCID 17938208HCID 17938208, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

229.405 g (696.6 mmol) of 3,4-bis(2-methylbutyloxy)-1-bromobenzene, 215 g (731 mmol) of 3,4-bis(2-methylbutyloxy)benzeneboronic acid and 202.1 g (1.462 mol) of K2CO3 were suspended in 800 ml of toluene and 800 ml of water and the mixture was saturated with N2 for 1 hour. 1.74 g (1.505 mmol) of Pd(PPh3)4 was subsequently added under protective gas. The turbid, slightly yellowish mixture was stirred vigorously under reflux for about 7 hours under nitrogen. After cooling, the organic phase was stirred with 500 ml of 1% strength NaCN solution. The phases were separated and the organic phase was washed with water, dried over Na2SO4 and evaporated on a rotary evaporator. This gave 339 g (679.7 mmol, 98%) of a light-brown oil which, according to 1H NMR, had a purity of 97% and was used directly in the subsequent reaction.

Workup

  1. temperatureunder reflux for about 7 hours under nitrogen
  2. temperatureAfter cooling
  3. customThe phases were separated
  4. washthe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated on a rotary evaporator
  7. customwas used directly in the subsequent reaction

Sources & evidence

ORD record
ord-6406ac251d864a948edc7e1c09cd3eec
Source dataset
uspto-grants-2007_10
Patent number
US07288617B2

Reaction notes

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