Phosphorus tribromide → 2-Benzyloxy-6-bromomethyl-naphthalen

HRID 48101Notes

Reaction equation

HRID 48101 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19]O)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:22]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][Br:22])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 21976870[6-(Benzyloxy)naphthalen-2-yl]methanol

Product 1

HCID 219769172-Benzyloxy-6-bromomethyl-naphthalen

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-benzyloxy-naphthalen-2-yl)-methanol (17) (1 equi.) in CH2Cl2 (4 mL/mmole), a solution of phosphorus tribromide (4 mL/mmole), (0.4 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) and recrystallization from acetonitrile afforded 2-benzyloxy-6-bromomethyl-naphthalene (18) a white solid (92%).

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography
  7. customon silica gel (dichloromethane) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-8ad635f40531461aa37ff1b7c9df0ea0
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Reaction notes

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