Phosphorus tribromide → 1-(Bromomethyl)-4-octylbenzene

HRID 710366Notes

Reaction equation

HRID 710366 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]O)=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>CCOCC>[CH2:5]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][Br:2])=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 14763613(4-Octylphenyl)methanol

Product 1

HCID 137451541-(Bromomethyl)-4-octylbenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step B (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.57 (m, 2H); 2.57 (tr, 2H, J=7.9 Hz); 4.48 (s, 2H); 7.13 (d, 2H, J=8 Hz); 7.28 (d, 2H, J=8 Hz).

Workup

  1. additionThis was poured onto ice (5 g)
  2. extractionthe product was extracted with fresh Et2O (2×10 ml)
  3. washThe combined extracts were washed with 5% NaHCO3, H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue was purified by FCC (SiO2, hexane)

Sources & evidence

ORD record
ord-2180e73a167044a199c139d49ece5ab3
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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