Phosphorus tribromide → 2-(Bromomethyl)-6-fluoronaphthalene

HRID 333229Notes

Reaction equation

HRID 333229 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12]O)[CH:6]=[CH:5]2.P(Br)(Br)[Br:15]>C(Cl)Cl>[Br:15][CH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58954787(6-Fluoronaphthalen-2-yl)methanol

Product 1

HCID 5946332-(Bromomethyl)-6-fluoronaphthaleneYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-fluoro-naphthalen-2-yl)-methanol (2.0 g, 11.3 mmol) in CH2Cl2 (30 mL) was added PBr3 (1.0 M in CH2Cl2, 22.6 mmol). The reaction mixture was stirred for 3 h at room temperature before being quenched by NH4Cl (30 mL). The organic layer was separated, dried and concentrated. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:10) to afford 2-bromomethyl-6-fluoro-naphthalene (2.23 g, 74%).

Workup

  1. custombefore being quenched by NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:10)

Sources & evidence

ORD record
ord-d8abc23c2dda45158b33302e8b32cff6
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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