Epichlorohydrin → HCID 67508106, compound

HRID 1400018Notes

Reaction equation

HRID 1400018 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][CH:13]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>C1COCC1>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:19]#[N:20])[CH2:21][CH:23]2[CH2:24][OH:25])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 27914Benzeneacetonitrile, 4-bromo-HCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 67508106HCID 67508106, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of NaHMDS (23 g, 127.5 mmol) in THF (80 mL), was added a solution of 4-bromophenylacetonitrile (10 g, 51.0 mmol) in THF (80 mL) at −10° C. and stirred for 10 min. Epichlorohydrin (4.7 mL, 56.11 mmol) was added to the reaction mixture at −10° C. and then stirred the mixture at r.t. for 4 h. After completion of the reaction as indicated by TLC, the reaction mixture was quenched with 2:1 dioxane:hydrochloric acid (10 mL) at 0° C. and extracted with diethyl ether (3×200 mL). The combined organic layers were dried over anhydrous sodium sulphate and concentrated to yield the title compound (12.8 g, 100%) as brown oil which was used as such in the next step.

Workup

  1. stirringstirred the mixture at r.t. for 4 h
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with 2:1 dioxane
  4. extractionhydrochloric acid (10 mL) at 0° C. and extracted with diethyl ether (3×200 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc678e209e684631ab9e07ec2eb6ec69
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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