Diethyl Ether → 3-(2-Bromo-phenoxy) acrylic acid methyl ester
Reaction equation
[C:1]([O:5][CH2:6]C)(=[O:4])[C:2]#[CH:3].C(N(CC)CC)C.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].CCOCC>C1COCC1>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[Br:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirring solution of 972 mg (11.56 mmol) of ethyl propiolate in 20 mL of THF at 0° C. is added a solution of 1.61 mL (11.56 mmol) of triethylamine in 5 mL of THF, followed by a solution of 2.0 g (11.56 mmol) of 2-Bromophenol in 5 mL of THF. The resulting clear orange-brown solution is stirred 5 h at 0° C., then poured into 100 mL of Et2O and extracted with H2O (1×100 mL). The organic layer is separated and washed with sat. Na2CO3 (1×100 mL), dried (MgSO4), and the solvent removed in vacuo to provide 2.97 g of the title compound as an orange oil which is used without any further purification: 1H NMR (CDCl3, 300 MHz) δ7.71 (d, 1H, J=12.3), 7.61 (d, 1H, J=7.4), 7.37-7.08 (m, 3H), 5.47 (d, 1H, J=12.3), 3.72 (s, 3H); Rf =0.40 in hexane/EtOAc 5/1.
Workup
- extractionextracted with H2O (1×100 mL)
- customThe organic layer is separated
- washwashed with sat. Na2CO3 (1×100 mL)
- dry with materialdried (MgSO4)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-e67462d79c6c421fbb7101452520faec
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859007
Reaction notes
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