4-Bromophenol → 3-Methyl-but-2-enoic acid 4-bromo-phenyl ester

HRID 51661

Reaction equation

HRID 51661 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15].C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O.CCCCCC>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14](=[O:15])[CH:13]=[C:12]([CH3:17])[CH3:11])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 78084-BromophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 7337973-Methyl-but-2-enoic acid 4-bromo-phenyl esterYield 59%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred, cooled (ice bath) suspension of sodium hydride (2.4 g, 100 mmol) in anhydrous tetrahydrofuran (200 mL), 4-bromo phenol (17.3 g, 100 mmol) was added followed by 3,3,-dimethyl acryloyl chloride (11.14 mL, 100 mmol). After 4 hours at ambient temperature, the reaction mixture was poured into brine and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 2% ethyl acetate in hexane as the eluent to afford the title compound (15 g, 59%).

Workup

  1. temperatureTo a stirred, cooled
  2. additionwas added
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford an oil which

Sources & evidence

ORD record
ord-617a67e1a15a474a9a2787df791f3888
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Linked notes

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