Boron tribromide → HCID 19918016, compound

HRID 1755844Notes

Reaction equation

HRID 1755844 reaction equation
C([O:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:15][O:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[O:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[OH:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:15][O:16][N:17]2[C:18](=[O:27])[C:19]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]3[C:21]2=[O:22])[O:13][CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19917924HCID 19917924, compound

Product 1

HCID 19918016HCID 19918016, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

N-[[5-(Benzyloxy)-4-oxo-4H-pyran-2-yl]methoxy]-phthalimide (1.77 g) (4.7 mmol) are suspended in 250 ml of dichloromethane and treated at -70° C. with 1.32 g (5.2 mmol) of boron tribromide (dissolved in 5 ml of dichloromethane). The mixture is stirred at -70° C. for 3 hours and at room temperature for 20 hours. The solvent is removed in a vacuum and the residue is treated at 0° C. with about 70 ml of water and 10 ml of ethanol. After stirring for 2 hours the product is filtered off and washed in succession with water, ethanol and diethyl ether. There are obtained 1.3 g of N-[(5-hydroxy-4-oxo-4H-pyran-2-yl)methoxy]phthalimide as a white powder of m.p. 200°-203° C. (dec.).

Workup

  1. customThe solvent is removed in a vacuum
  2. additionthe residue is treated at 0° C. with about 70 ml of water and 10 ml of ethanol
  3. stirringAfter stirring for 2 hours the product
  4. filtrationis filtered off
  5. washwashed in succession with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-a61b7da421e340688be504a879cb9afc
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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