Potassium Hydroxide → 2-bromo-6-nitrobenzyl (2E)-but-2-en-1-yl ether

HRID 2173267Notes

Reaction equation

HRID 2173267 reaction equation
[OH-:1].[K+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13]Br>C(O)/C=C/C>[CH2:9]([O:1][CH2:13][C:5]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=1[Br:3])/[CH:4]=[CH:5]/[CH3:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzene

Product 1

HCID 866930082-bromo-6-nitrobenzyl (2E)-but-2-en-1-yl ether

Reagents, catalysts & solvents 1

HCID 637922trans-Crotyl alcoholSolvent

Procedure

To a solution of KOH (0.57 g, 0.099 mol) in (2E)-but-2-en-1-ol (100 mL) was added 1-bromo-2-(bromomethyl)-3-nitrobenzene (10 g, 0.033 mol), and the mixture was stirred at r.t for 30 min. Then the mixture was washed with water (200 mL*4), extracted with EtOAc, dried over Na2SO4, concentrated in vacuo. The residue was purified via chromatography (petrol ether) to give 2-bromo-6-nitrobenzyl (2E)-but-2-en-1-yl ether. 1H-NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.0 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.25˜7.30 (m, 1H), 5.68˜5.77 (m, 1H), 5.51˜5.58 (m, 1H), 4.82 (s, 2H), 1.69 (d, J=6.0 Hz, 3H).

Workup

  1. washThen the mixture was washed with water (200 mL*4)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via chromatography (petrol ether)

Sources & evidence

ORD record
ord-8590d9df07b647188215389abfa57a8a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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