Triethylamine → Ether phthalimide

HRID 1612570Notes

Reaction equation

HRID 1612570 reaction equation
C(N(CC)CC)C.Br[CH2:9][CH2:10][O:11][CH2:12][C:13]1C=CC=CC=1F.O[N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CN1CCCC1=O>[C:25]1(=[O:26])[NH:21][C:22](=[O:31])[C:23]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]12.[CH3:9][CH2:10][O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 233530971-Bromo-2-(2-fluorobenzyloxy)-ethane

Product 1

HCID 18959638Ether phthalimideYield 119.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

At 20° to 25° C. and over a period of 1 hour, 108 ml of triethylamine was dripped into a mixture of 165 g (0.71 mol) of 1-bromo-2-(2-fluorobenzyloxy)-ethane, 116 g (0.7 mol) of N-hydroxyphthalimide and 710 ml of N-methyl-2-pyrrolidone. After the mixture had been kept for 5 hours at 60° C., the cold mixture was poured into 2000 ml of ice water, the precipitate was suction filtered, washed with water and isopropanol and dried under reduced pressure over phosphorus pentoxide. There was obtained 185 g (82%) of phthalimide ether, m.p. 62°-64° C. 1H-NMR (250 MHZ, d6 -DMSO): δ=3.85 (m,2H), 4.35 (m,2H), 4.54 (s,2H), 7.10-7.40 (m,4H), 7.88 (s,4H).

Workup

  1. waitAfter the mixture had been kept for 5 hours at 60° C.
  2. filtrationfiltered
  3. washwashed with water and isopropanol
  4. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-a43b7d7b3ae14491b541658f6815adb3
Source dataset
uspto-grants-1993_03
Patent number
US05190573

Reaction notes

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