Methyl 4-(bromomethyl)benzoate → HCID 18510220, compound

HRID 1371014Notes

Reaction equation

HRID 1371014 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][Si](C)(C)C)[C:9]#N)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.BrC[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH3:35][O:34][C:32](=[O:33])[C:31]1[CH:36]=[CH:37][C:28]([CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:11])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 2724141Tetrabutylammonium FluorideHCID 2733832Lithium HexamethyldisilazideHCID 117155522-(4-Fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile

Product 1

HCID 18510220HCID 18510220, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

To 2-(4-fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile (0.500 g, 2.24 mmol) in degassed THF (11 ml) at −78° C. was added LHMDS 1M in THF (2.4 ml). To the previous reaction mixture a solution of methyl 4-(bromomethyl)benzoate (0.513 g, 2.25 mmol) in THF (2 ml) was then added. After a period of 1 h at r.t., tetrabutylammonium fluoride solution 1 M in THF (2.23 ml) was added to the reaction mixture and stirred for 10 minutes. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 30% giving 0.4 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8d0496ff676b429dbd0e273701dac41f
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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