Phosphorus tribromide → 1-(Bromomethyl)-3-(2-methoxyethoxy)benzene

HRID 1685125Notes

Reaction equation

HRID 1685125 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12]O)[CH:9]=[CH:10][CH:11]=1.P(Br)(Br)[Br:15]>C(Cl)Cl>[Br:15][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20110194[3-(2-Methoxyethoxy)phenyl]methanol

Product 1

HCID 431416981-(Bromomethyl)-3-(2-methoxyethoxy)benzeneYield 171.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 27C (18.2 g, 100 mmol) in CH2Cl2 (300 mL) was added PBr3 (4.5 mL, 48 mmol) at 0° C., then the resulting mixture was allowed to warm to RT overnight. The reaction mixture was quenched with saturated NaHCO3 (50 mL) and stirred at RT for an addition 0.5 h. The mixture was extracted with CH2Cl2, and the combined extracted were dried (MgSO4), filtered, and evaporated in vacuum to give the product as a yellow oil (20.2 g, 82%, two steps). 1H NMR (300 MHz, CDCl3): δ 3.45 (s, 1H), 3.75 (t, 2H, J=4.8 Hz), 4.12 (t, 2H, J=4.8 Hz), 4.45 (s, 2H), 6.85-6.99 (m, 3H), 7.21-7.26 (m, 1H). LC-MS: purity >95%, ESI-MS: M/Z 245 (M+H)+, 247 (M+2+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 (50 mL)
  2. extractionThe mixture was extracted with CH2Cl2
  3. extractionthe combined extracted
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-74671257e2f14c23a007d545bfa40b15
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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