Hydrogen Bromide → 1,8-Bis(bromomethyl)naphthalene

HRID 472988Notes

Reaction equation

HRID 472988 reaction equation
[C:1]1([CH2:13]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11]O)[CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.P(Br)(Br)[Br:19].[BrH:22]>O>[Br:22][CH2:13][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][Br:19])[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 24614Phosphorus tribromideHCID 748461,8-Naphthalenedimethanol

Product 1

HCID 2912081,8-Bis(bromomethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of naphthalene-1,8-diyldimethanol (1.15 g, 6 mmol) and CH2Cl2 (10 mL) was stirred mechanically and PBr3 (1.2 mL) added dropwise over 20 mins. During the first half of the addition the solution refluxed spontaneously. After stirring overnight at room temperature, water was added dropwise with stirring over 20 min, which again caused refluxing and evolution of much HBr. After stirring for an additional 2 h, water was added and the layers separated and the organic layer washed with water. The organic layer was evaporated in vacuum to give the crude product, which was used directly without purification (1.6 g, 84%). 1H-NMR (CDCl3): 5.30 (s, 4H), 7.44 (m, 2H), 7.62 (m, 2H), 7.87 (m, 2H).

Workup

  1. additionDuring the first half of the addition the solution
  2. temperaturerefluxed spontaneously
  3. stirringAfter stirring overnight at room temperature
  4. stirringwith stirring over 20 min
  5. temperaturewhich again caused refluxing
  6. stirringAfter stirring for an additional 2 h
  7. customthe layers separated
  8. washthe organic layer washed with water
  9. customThe organic layer was evaporated in vacuum

Sources & evidence

ORD record
ord-f820e9f3736e4563914ba89a2d9449c3
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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