Ethyl bromoacetate → (4-Benzyloxy-2-vinylphenoxy)acetic Acid Ethyl Ester

HRID 898462Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]=[CH2:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH:16]=[CH2:17])[CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

4-Benzyloxy-2-vinylphenol (0.40 g, 1.77 mmol) was dissolved in anhydrous DMF (4 mL), followed by the addition of ethyl bromoacetate (0.29 mL, 2.65 mmol), and cesium carbonate (0.75 g, 2.30 mmol). The mixture was then heated for 18 h (55° C.). The reaction mixture was then cooled and concentrated in vacuo. The crude residue was partitioned between EtOAc (70 mL) and water (40 mL). The organic layer was washed with brine, dried (Na2SO4), and removed in vacuo to give 0.56 g (100%) of a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.44-7.31 (m, 4H), 7.13 (d, J=2.9 Hz, 1H), 7.10-7.06 (m, 1H), 6.82 (dd, J=8.8, 2.9 Hz, 1H), 6.73 (d, J=9.3 Hz, 1H), 5.76 (dd, J=17.1 Hz, 1.5 Hz, 1H), 5.30 (dd, J=11.2, 1.5 Hz, 1H), 5.03 (s, 2H), 4.58 (s, 2H), 4.26 (q, J=7.2 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H); MS (FIA) m/e 313 (M+1).

Workup

temperatureThe reaction mixture was then cooled
concentrationconcentrated in vacuo
customThe crude residue was partitioned between EtOAc (70 mL) and water (40 mL)
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
customremoved in vacuo

Sources & evidence

ORD record: ord-13c83b029b2c4fde8db09ef4814de807
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351728B2

Reaction notes

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