Allyl bromide → 2-(Allyloxymethyl)-1-fluoro-3-iodobenzene

HRID 1363155Notes

Reaction equation

HRID 1363155 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[CH2:9][OH:10].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>C1COCC1>[CH2:15]([O:10][CH2:9][C:3]1[C:4]([I:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 59705003(2-Fluoro-6-iodophenyl)methanol

Product 1

HCID 597050162-(Allyloxymethyl)-1-fluoro-3-iodobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-fluoro-6-iodophenyl)methanol (10 mmol) in 50 mL of THF was added NaH (12 mmol) in small portions at room temperature. After the addition, allylbromide (12 mmol) was added slowly via syringe. The reaction mixture was stirred 16 hours at room temperature. The resulting white heterogeneous mixture was quenched with water and then diluted with 100 mL of Et2O, followed by washing with water and brine. The organic layer was dried over MgSO4 and then concentrated to dryness in vacuo to offer 2.8 g of the title compound.

Workup

  1. additionwas added slowly via syringe
  2. customThe resulting white heterogeneous mixture was quenched with water
  3. additiondiluted with 100 mL of Et2O
  4. washby washing with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-2f2efadf26944589a7d9958c1dac0d17
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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