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

HRID 1169942Notes

Reaction equation

HRID 1169942 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 97%

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 (6.8 g, 9.7 mmol) as a yellow liquid in 97% yield. 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-01fae2781adf41758c06aa5cb1f61e94
Source dataset
uspto-grants-2010_11
Patent number
US07825160B2

Reaction notes

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