3-Buten-1-ol → HCID 66688391, compound

HRID 238480Notes

Reaction equation

HRID 238480 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1Br)([CH3:4])([CH3:3])[CH3:2].[CH2:15]([OH:19])[CH2:16][CH:17]=[CH2:18]>CC([O-])=O.CC([O-])=O.[Pd+2].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.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH:18]=[CH:17][CH2:16][CH2:15][OH:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 693893-Buten-1-olHCID 2385872-Bromo-1-tert-butyl-4-nitrobenzene

Product 1

HCID 66688391HCID 66688391, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mix of 1-(tert-butyl)-2-bromo-4-nitrobenzene (3.652 g), TEA (5.92 ml), 3-buten-1-ol (5.48 ml), Pd(OAc)2 (32 mg), Pd(PPh3)4 (327 mg) and toluene (40 ml) was degassed with nitrogen and heated in a sealed vessel for 16 h at 120° C. The next day, the reaction mixture was cooled to RT, filtered, and concentrated in vacuo. The crude was eluted on a silica gel column with 15% to 22% EtOAc/hexanes gradient system to yield a yellow-brown oil.

Workup

  1. customwas degassed with nitrogen
  2. temperatureThe next day, the reaction mixture was cooled to RT
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe crude was eluted on a silica gel column with 15% to 22% EtOAc/hexanes gradient system
  6. customto yield a yellow-brown oil

Sources & evidence

ORD record
ord-65cdf4843e424619bae027e2bf1b6106
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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