Allyl bromide → 13990-72-2

HRID 2069689Notes

Reaction equation

HRID 2069689 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][CH:13]=[CH2:14]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:13]=[CH2:12]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 97324-FluorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 63734213990-72-2Yield 97.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorophenol (22.4 g, 200 mmol) in DCM (200 mL) was added 50% NaOH (aq) (100 mL), 3-bromoprop-1-ene (26.0 mL, 300.0 mmol) and tetra-n-butylammonium bromide (1.90 g, 6.0 mmol). The suspension was stirred at room temperature for 24 h. The layers were separated and washed with water (2×100 mL), brine (100 mL) and dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (0-20% EtOAc in hexanes) to provide the desired 1-(allyloxy)-4-fluorobenzene (852) (29.7 g, 97.8%) as a colorless oil.

Workup

  1. customThe layers were separated
  2. washwashed with water (2×100 mL), brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e79c596f88aa4988966e37c036736688
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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