Ethyl bromoacetate → HCID 66713200, compound

HRID 2060478Notes

Reaction equation

HRID 2060478 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, 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-8abd00ffcaef48ff96bf1f6d9dc0b916
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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