Triphenylphosphine → 1-(Bromomethyl)naphthalene

HRID 343101

Reaction equation

HRID 343101 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[C:22]1([CH2:32]O)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:32][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 209081-NaphthalenemethanolHCID 24408Bromine

Product 1

HCID 1378441-(Bromomethyl)naphthaleneYield 95.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 912 mg (3.48 mmol, 1.2 equiv) of triphenylphosphine in 10 mL of CCl4 at 0° C. is added 180 μL (3.48 mmol, 1.2 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 500 mg (3.16 mmol) of 1-Naphthalenemethanol in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 1.5 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 10/1 as eluent afforded 670 mg of the title compound as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) δ8.18 (d, 1H), 7.83 (m, 2H), 7.63-7.38 (m, 4H), 4.98 (s, 2H); Rf =0.65 in hexane/EtOAc 5/1.

Workup

  1. stirringThe resulting solution is stirred 1.5 h at RT
  2. customthe solvent is removed in vacuo
  3. customPurification of the residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-1d7a76cccb7d4350a53347a6e7315561
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Linked notes

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