Water → (Z)-ethyl 4-(N-(2,4-dibromo-6-fluoro-3-methoxyphenyl)acetamido)but-2-enoate

HRID 1404088Notes

Reaction equation

HRID 1404088 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Br:10])[CH:5]=[C:4]([F:11])[C:3]=1[NH:12][C:13](=[O:15])[CH3:14].[H-].[Na+].Br[CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Br:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]([CH2:19]/[CH:20]=[CH:21]\[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5373944Ethyl (E)-4-bromobut-2-enoateHCID 86654326HCID 86654326, compound

Product 1

HCID 86654327(Z)-ethyl 4-(N-(2,4-dibromo-6-fluoro-3-methoxyphenyl)acetamido)but-2-enoateYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 8-6 (1.3 g, 3.82 mmol) in THF (20 mL) at room temperature was added NaH (100 mg, 4.2 mmol, dispersed in mineral oil, 60%). The mixture was stirred for 30 min until no gas was released. (E)-ethyl 4-brombut-2-enoate (0.88 g, 4.58 mmol) in THF (5 mL) was added. The mixture was stirred overnight at room temperature. TLC showed that the reaction was completed. Water was added to the reaction mixture and extracted with ethyl acetate (50 mL×3). The combined organic layers were combined and were concentrated in vacuo. The residue was purified by flash chromatography (silica gel, elution with ethyl acetate/petroleum=1:8 to 1:2) to afford 8-7 (1.6 g, 92.4%) as yellow oil.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. concentrationwere concentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica gel, elution with ethyl acetate/petroleum=1:8 to 1:2)

Sources & evidence

ORD record
ord-28e205f06596476f93e84ab9070844c6
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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