2-(3-Benzyloxy-5-bromophenyl)malonic acid tert-butyl ester ethyl ester → (3-Benzyloxy-5-bromophenyl)-acetic acid ethyl ester

HRID 426303Notes

Reaction equation

HRID 426303 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1)C(OC(C)(C)C)=O)[CH3:2]>CC(O)=O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:14]=1)[CH3:2]

Participants

3

Reactant 1

HCID 667024822-(3-Benzyloxy-5-bromophenyl)malonic acid tert-butyl ester ethyl ester

Product 1

HCID 66702483(3-Benzyloxy-5-bromophenyl)-acetic acid ethyl esterYield 194.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(3-Benzyloxy-5-bromophenyl)malonic acid tert-butyl ester ethyl ester (7.2 g, contains 1.4 equivalent malonic acid tert-butyl ester ethyl ester, 10 mmol) was dissolved in glacial AcOH (50 mL) and heated to reflux for 12 h. The AcOH was removed under reduced pressure. The residue was poured into Na2CO3 solution (sat aq) and the mixture was extracted with EtOAc (×3). The combined organic extracts were washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure to give (3-benzyloxy-5-bromo-phenyl-)acetic acid ethyl ester as a yellow liquid yield 6.8 g (97%). 1H NMR (CDCl3) δ 7.44-7.30 (m, 5H), 7.07-7.03 (m, 2H), 6.87-6.84 (m, 1H), 5.03 (s, 2H), 4.15 (q, 2H), 3.54 (s, 2H), 1.26 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. customThe AcOH was removed under reduced pressure
  4. additionThe residue was poured into Na2CO3 solution (sat aq)
  5. extractionthe mixture was extracted with EtOAc (×3)
  6. washThe combined organic extracts were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd1343454b7f46c4aee1c886812d074d
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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