Sodium hydride → 4-Bromocinnamonitrile

HRID 431779

Reaction equation

HRID 431779 reaction equation
[H-].[Na+].P(=O)([O-])O[C:5](CC)(CC)[C:6]#[N:7].[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH:5][C:6]#[N:7])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707414-BromobenzaldehydeHCID 178449162HCID 178449162, compound

Product 1

HCID 534804-Bromocinnamonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 60% suspension of NaH in mineral oil (2.16 g, 54.1 mmol) was suspended in THF (50 ml) and cooled to 0° C. under nitrogen. Diethyl-cyanomethyl phosphonate (8.74 ml, 54.1 mmol) was added dropwise and the whole stirred at 0° C. for 30 min. 4-bromobenzaldehyde (10 g, 54.1 mmol) was then added dropwise as a solution in 20 ml THF, and the mixture allowed to warm to room temperature overnight. The reaction was quenched with water, extracted with EtOAc (3×50 ml), dried (MgSO4) and then filtered and evaporated to a yellow oil. This oil was taken up in a 9:1 mixture of pentane:EtOAc from which the title product crystallised (5.8 g, 52%); 1HNMR (400 MHz, CDCl3) δ: 5.82 (d, 1H), 7.21-7.28 (m, 3H), 7.50 (d, 2H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. additionThis oil was taken up in a 9:1 mixture of pentane
  8. customEtOAc from which the title product crystallised (5.8 g, 52%)

Sources & evidence

ORD record
ord-3bcbe19b883f47869f4037be1b4f4d49
Source dataset
uspto-grants-2003_12
Patent number
US06660756B2

Linked notes

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