Sodium Hydroxide → 1-(Bromomethyl)naphthalene

HRID 1181840Notes

Reaction equation

HRID 1181840 reaction equation
[C:1]1([CH2:11]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:14].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)Cl>[Br:14][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 209081-NaphthalenemethanolHCID 24614Phosphorus tribromideHCID 516892Sodium Bicarbonate

Product 1

HCID 1378441-(Bromomethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-naphthylmethanol (3.2 g) was taken up in CH2Cl2 (10 mL) and cooled to 0° C. Phosphorus tribromide (25 mL, 1 M in CH2Cl2) was added drop wise and allowed to stir at RT for 2 h. Saturated sodium bicarbonate and sodium hydroxide was added slowly until alkaline. The organic layer was separated, dried over sodium sulfate, and evaporated under reduced pressure to give an off-white solid (4.4 g). Proton NMR was sufficient for the next step.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-40656a05150d4271840c7b83afc0b12a
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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