Ethyl bromoacetate → HCID 66713200, compound

HRID 1406171Notes

Reaction equation

HRID 1406171 reaction equation
[C:1]1(=[O:15])[C:9]2[CH:8]=[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]3=[CH:5][C:4]=2[C:3](=[O:14])[NH:2]1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)[CH3:17]>>[CH2:16]([O:18][C:19](=[O:22])[CH2:20][N:2]1[C:3](=[O:14])[C:4]2[CH:5]=[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]3=[CH:8][C:9]=2[C:1]1=[O:15])[CH3:17]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 3351942,3-Naphthalenedicarboximide

Product 1

HCID 66713200HCID 66713200, compound

Procedure

2 g (10.1 mmol) Benzo[f]isoindole-1,3-dione was reacted with bromoacetic acid ethyl ester analogously to Example D-21a. The crude product obtained was partitioned between ethyl acetate and water. Organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to give 2.68 g (9.5 mmol) of product. 1H NMR (200 MHz, CDCl3) δ 8.36 (s, 2 H), 8.05 (m, 2 H), 7.68 (m, 2 H), 4.49 (s, 2 H), 4.22 (q, J=7.0 Hz, 2 H), 1.29 (t, 7.0 Hz, 3 H).

Workup

  1. customThe crude product obtained
  2. customwas partitioned between ethyl acetate and water
  3. washOrganic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-dea3946aa56143c19bd22809a2efa43b
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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