Phosphorus tribromide → 4-Bromo-2-(bromomethyl)-1-methoxybenzene

HRID 391416Notes

Reaction equation

HRID 391416 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8]O)[CH:7]=1.[Br:12]P(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8][Br:12])[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 6122985-Bromo-2-methoxybenzyl alcohol

Product 1

HCID 49627394-Bromo-2-(bromomethyl)-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mmol) in dichloromethane (10 mL) at 0° C. was added tribromophosphine (1 M in dichloromethane, 9.2 mL, 9.2 mmol). The ice bath was removed and the reaction stirred for 15 min. The reaction was concentrated, poured onto cold saturated sodium bicarbonate, extracted with pentane, dried over magnesium sulfate, and concentrated to give 1.15 g (89%) as a white crystalline solid. 1H NMR (500 MHz, CDCl3) δ ppm 7.44 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.9, 6.1 Hz, 1H), 4.47 (s, 2H), 3.87 (s, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 156.7, 133.6, 132.8, 128.4, 112.8, 112.7, 56.0, 27.5.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. additionpoured onto cold saturated sodium bicarbonate
  4. extractionextracted with pentane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give 1.15 g (89%) as a white crystalline solid

Sources & evidence

ORD record
ord-39fe08d9204e45ffbf2022f5065b2026
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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