Allyl bromide → HCID 67179112, compound

HRID 1807948Notes

Reaction equation

HRID 1807948 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[CH2:14](Br)[CH:15]=[CH2:16]>O1CCCC1>[CH2:16]([O:13][C:10]([C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1)([CH3:11])[CH3:12])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 6377332-(4-Fluorophenyl)-2-propanol

Product 1

HCID 67179112HCID 67179112, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of sodium hydride (1.47 g) in dry tetrahydrofuran (60 ml) was added dropwise under an argon atmosphere a solution of 2-(4-fluorophenyl)-2-propanol (4.35 g) in dry tetrahydrofuran (10 ml). The resulting yellow suspension was stirred at room temperature for 10 min. A solution of allyl bromide (3.1 ml) diluted in dry tetrahydrofuran (10 ml) was added slowly. The reaction mixture was stirred for 30 min and quenched by addition of water. The solution was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4) and evaporated. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->90:10) to give 1-(1-allyloxy-1-methyl-ethyl)-4-fluoro-benzene (3.30 g, 60%) as a light yellow liquid. MS (EI): 179.0 ([M-CH3]).

Workup

  1. additionwas added slowly
  2. stirringThe reaction mixture was stirred for 30 min
  3. customquenched by addition of water
  4. extractionThe solution was extracted with ethyl acetate twice
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->90:10)

Sources & evidence

ORD record
ord-669736b2c24c454fb7e29a144a0dbc01
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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