Carbon tetrabromide → {[(8-Bromooctyl)oxy]methyl}benzene

HRID 1472294Notes

Reaction equation

HRID 1472294 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11481775HCID 11481775, compound

Product 1

HCID 15148292{[(8-Bromooctyl)oxy]methyl}benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 2 (133 g, 0.5635 mol) was dissolved in 1.5 L of DCM, CBr4 (280.35 g, 0.8456 mol) was added to this stirring solution and the reaction mixture was cooled to 0° C. under an inert atmosphere. PPh3 (251.03 g, 0.9571 mol) was then added in portions maintaining the temperature below 20° C. and after complete addition, the reaction mixture was stirred for 3 hours at room temperature. After completion of reaction, solid (PPh3O) precipitated out from the reaction mixture was isolated by filtration and the filtrate was diluted with crushed ice (˜1.5 kg) and extracted with DCM (3×750 mL). The organic layer was separated, dried over anhydrous Na2SO4 and distilled under vacuum. The resulting crude compound was chromatographed on 60-120 mesh silica gel column using 0-5% ethyl acetate in hexanes as eluting system to afford compound 3 (150 g, 89%) as pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ=7.33-7.25 (m, 5H), 4.49 (s, 2H), 3.47-3.41 (m, 2H), 3.41-3.37 (m, 2H), 1.86-1.80 (m, 4H), 1.62-1.56 (m, 2H), 1.42-1.29 (m, 8H).

Workup

  1. temperaturemaintaining the temperature below 20° C.
  2. additionafter complete addition
  3. customAfter completion of reaction, solid (PPh3O)
  4. customprecipitated out from the reaction mixture
  5. customwas isolated by filtration
  6. extractionextracted with DCM (3×750 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous Na2SO4
  9. distillationdistilled under vacuum
  10. customThe resulting crude compound was chromatographed on 60-120 mesh silica gel column
  11. washas eluting system

Sources & evidence

ORD record
ord-77760795fca2499692b31e0466733b8a
Source dataset
uspto-grants-2015_04
Patent number
US09012498B2

Reaction notes

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