Butyl bromide → HCID 13791776, compound

HRID 1799358Notes

Reaction equation

HRID 1799358 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[OH:24].[CH2:25](Br)[CH2:26][CH2:27][CH3:28]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(O)C>[CH2:25]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[O:24][CH2:13][CH2:4][CH2:5][CH3:6])[CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 3

HCID 8002Butyl bromideHCID 11762BinolHCID 14798Sodium Hydroxide

Product 1

HCID 13791776HCID 13791776, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.0 g NaOH, 20 ml water and 2.8 g 2,2′-dihydroxy-1,1′-binaphthyl prepared in the step a) of the Example 19 are added to a round bottom flask with the volume of 100 mL and are then stirred to be dissolved, 4.1 g n-butyl bromine, 0.2 g tetrabutylammonium bromide and 10 ml ethanol are dropwise added to the round bottom flask, the temperature of the water bath is maintained at 70° C., and after the reaction is performed for 4 hours, the reaction product is poured, while hot, into 50 g crushed ice, followed by stirring to further separate crystal out. The crystal is filtered the filter cake is washed with alkali solution and icy water to obtain light yellow granular solid. The solid is recrystallized with ethanol to obtain yellow-white crystal 2,2′-dibutoxy-1,1′-binaphthyl with the yield of 92.3%, the melting point of 85° C. and the content, according to HLPC detection, of 96.6%.

Workup

  1. additionare added to a round bottom flask with the volume of 100 mL
  2. dissolutionto be dissolved
  3. additionthe reaction product is poured
  4. customwhile hot, into 50 g crushed ice
  5. stirringby stirring
  6. customto further separate crystal out
  7. filtrationThe crystal is filtered the filter cake
  8. washis washed with alkali solution and icy water
  9. customto obtain light yellow granular solid
  10. customThe solid is recrystallized with ethanol

Sources & evidence

ORD record
ord-b6e849b264d345879de928bff56e66b4
Source dataset
uspto-grants-2013_01
Patent number
US08344080B2

Reaction notes

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