Benzyl Bromide → HCID 66746793, compound

HRID 331697Notes

Reaction equation

HRID 331697 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([CH:15]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[C:13]([C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 12686974HCID 12686974, compoundHCID 178418339Butyllithium

Product 1

HCID 66746793HCID 66746793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of diisopropylamine (7.80 ml, 54.7 mmol) in 100 ml dry tetrahydrofuran at −78° C. was added n-butyl lithium (34.2 ml, 54.7 mmol) and stirred for 1 h while the reaction mixture was allowed to warm up to −40° C. A solution of ethyl 2-cyano-2-(3-methoxyphenyl)acetate (10 g, 45.6 mmol) in 100 ml dry tetrahydrofuran was added and the mixture stirred for 30 min. Then (bromomethyl)benzene (8.13 ml, 68.4 mmol) was added and the reaction was stirred over night. The solvent was evaporated and the residue dissolved in ethyl acetate, which was washed with 10% citric acid, water and brine. The combined organic layers were dried over sodium bicarbonate, filtered and the solvent evaporated to obtain a yellow-orange oil. Purification on 120 g SiO2 using 20% ethyl acetate in cyclohexene afforded a clear colourless oil m=9.4 g (66.6%).

Workup

  1. stirringthe mixture stirred for 30 min
  2. stirringthe reaction was stirred over night
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwhich was washed with 10% citric acid, water and brine
  6. dry with materialThe combined organic layers were dried over sodium bicarbonate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customto obtain a yellow-orange oil
  10. customPurification on 120 g SiO2 using 20% ethyl acetate in cyclohexene
  11. customafforded a clear colourless oil m=9.4 g (66.6%)

Sources & evidence

ORD record
ord-308d6ee8aa0e49088ee45042ba5cb4d1
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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