Ethyl bromoacetate → HCID 66713200, compound

HRID 1866357Notes

Reaction equation

HRID 1866357 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, 2H), 8.05 (m, 2H), 7.68 (m, 2H), 4.49 (s, 2H), 4.22 (q, J=7.0 Hz, 2H), 1.29 (t, 7.0 Hz, 3H).

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-0dc9b0c811cc4062a55bbd7b912e78be
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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