Boron tribromide → HCID 68726284, compound

HRID 493173Notes

Reaction equation

HRID 493173 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:14]=3[CH:15]=2)=[O:10])[CH2:3]1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:14]=3[CH:15]=2)=[O:10])[CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68726450HCID 68726450, compound

Product 1

HCID 68726284HCID 68726284, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above prepared ((cis)-2,6-dimethyl-morpholin-4-yl)-(5-methoxy-benzofuran-2-yl)-methanone (0.614 g, 2.12 mmol) was dissolved in 14 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (4.24 mL of 1M solution in CH2Cl2, 2 eq.). After 1 additional h at RT, the reaction mixture was carefully poured onto crashed ice, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/AcOEt=1/1) yielded 0.556 g of the title compound as off-white solid.

Workup

  1. additionAfter 1 additional h at RT, the reaction mixture was carefully poured
  2. extractiontwofold extracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f3912de0b29345438e84faa1194df7e8
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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