Water → HCID 68379630, compound

HRID 1410055Notes

Reaction equation

HRID 1410055 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([CH:9](P(=O)([O-])[O-])[F:10])=[C:5](CC)[C:4]=1[Br:17])C.[Li+].CC([N-]C(C)C)C.[CH:26]([C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)=O.O>C1COCC1>[Br:17][C:4]1[CH:5]=[C:6](/[C:9](/[F:10])=[CH:26]/[C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH:7]=[CH:8][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 2724682Lithium diisopropylamideHCID 131732207HCID 131732207, compound

Product 1

HCID 68379630HCID 68379630, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diethyl(3-bromophenyl)fluoromethylphosphonate (2.1 g, 6.5 mmol) in 50 mL of THF was added dropwise via syringe to a solution of LDA (5 mL, 10 mmol) in THF at −78° C. under N2 atmosphere. After 30 min at this temperature methyl 4-formylbenzoate (1.1 g, 6.5 mmol) in 50 mL of THF was added dropwise via syringe and then stirred at this temperature for 30 min and then allow warm to room temperature over 4 hours, and stirred overnight. The mixture was poured into H2O (300 mL) and then extracted with ethyl acetate (3×100 mL). The combined organic layer was concentrated and purified by silica gel chromatography (eluting with a mixture of petroleum ether and ethyl acetate=50:1) to give (Z)-methyl 4-(2-(3-bromophenyl)-2-fluorovinyl)benzoate (0.73 g, 33.6%) as a yellow oil.

Workup

  1. stirringstirred overnight
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. concentrationThe combined organic layer was concentrated
  4. custompurified by silica gel chromatography (
  5. washeluting with a mixture of petroleum ether and ethyl acetate=50:1)

Sources & evidence

ORD record
ord-2287b9c8e12246c1841eb7c49d1e0e6d
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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