Benzyl Bromide → HCID 89649135, compound

HRID 1773978Notes

Reaction equation

HRID 1773978 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:9]=[CH:10][CH3:11])=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(C)=O>CN(C=O)C.O>[CH2:14]([O:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[CH:9]=[CH:10][CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67880459HCID 67880459, compound

Product 1

HCID 89649135HCID 89649135, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-(propenyl)-phenol (mixture of E- and Z-isomer ca. 85:15) (1.10 g, 4.99 mmol, 1.0 eq.) in DMF (15 mL) was slowly added to sodium hydride 60% dispersion in mineral oil (261 mg, 6.52 mmol, 1.3 eq.) at 0° C. under N2. Upon completion of the addition, the mixture was allowed to warm to r.t. Benzyl bromide (0.61 mL, 4.99 mmol, 1.0 eq.) was added and the resulting mixture was stirred at r.t. for 18 hours. AcOEt was added and the reaction was stirred at r.t. for 30 min. Water was added to the mixture. The layers were separated and the org. phase was washed with water and sat. aq. NaCl soln., dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+10% AcOEt) to yield 2-benzyloxy-4-bromo-1-(propenyl)-benzene as a pale yellow oil as an unseparable mixture of E- and Z-isomers (ca. 9/1).

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction was stirred at r.t. for 30 min
  3. customThe layers were separated
  4. washphase was washed with water and sat. aq. NaCl soln
  5. dry with material, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane 100% to Heptane+10% AcOEt)

Sources & evidence

ORD record
ord-1cf0e348fd474f0a89f91f3f6c2bbf26
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

Loading…