Boron tribromide → HCID 71292918, compound

HRID 1404204Notes

Reaction equation

HRID 1404204 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]1[CH:18]=[N:17][CH:16]=[CH:15][N:14]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[N:14]1[CH:15]=[CH:16][N:17]=[CH:18][C:13]=1[CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[O:9]1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 71292840HCID 71292840, compound

Product 1

HCID 71292918HCID 71292918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(6-methoxy-chroman-2-yl)-pyrazine (663 mg, 2.74 mmol) in 50 ml of anhydrous dichloromethane was cooled to −10° C., and a solution of boron tribromide (9.6 ml of 1M solution in dichloromethane, 9.6 mmol) was added dropwise. After stirring at 0° C. for 1 h, 1 ml of boron tribromide solution was added and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched by slow addition of water, and after 10 min neutralized by addition of a sodium hydrogencarbonate solution. After decantation and extraction with dichloromethane, the organic layer was dried over sodium sulfate and concentrated in vacuo. After chromatography on silica gel (methanol in dichloromethane), 2-pyrazin-2-yl-chroman-6-ol was obtained as a yellow powder (625 mg, 100%).

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 1.5 h
  2. customThe reaction mixture was quenched by slow addition of water
  3. additionafter 10 min neutralized by addition of a sodium hydrogencarbonate solution
  4. extractionAfter decantation and extraction with dichloromethane
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aae0369d7d1e4665a3f278a68233d8d4
Source dataset
uspto-grants-2014_12
Patent number
US08912224B2

Reaction notes

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