Phosphorus tribromide → HCID 19861650, compound

HRID 1165415Notes

Reaction equation

HRID 1165415 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[C:7]([CH2:16]O)=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>C(OCC)C>[Br:5][C:6]1[C:7]([CH2:16][Br:2])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 264948(3-bromonaphthalen-2-yl)methanol

Product 1

HCID 19861650HCID 19861650, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

PBr3 (3.7 mL, 0.039 mol) was added dropwise to a suspension of 3-bromo-2-naphthalenyl methanol (8.55 g, 0.036 mol) and diethyl ether (80 mL) at 0° C. After 1 hour, the reaction was concentrated and partitioned between CH2Cl2 and H2O. The organic layer was separated and dried over MgSO4. Concentration in vacuo afforded 3-bromo-2-bromomethylnaphthalene as a crude product (10.6 g). The crude product was flash chromatographed on silica gel to afford the pure product as an off-white powder (6.0 g, m.p. 110°-111° C., yield 56%).

Workup

  1. concentrationthe reaction was concentrated
  2. custompartitioned between CH2Cl2 and H2O
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-95b623ee845b4e4bb3f70767464c035d
Source dataset
uspto-grants-1990_03
Patent number
US04910019

Reaction notes

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