Boron tribromide → HCID 86605500, compound

HRID 2103074Notes

Reaction equation

HRID 2103074 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[N:9]([C:15](=[O:17])C)[CH2:8][C:7]1([CH2:20][CH2:19][CH2:18]1)[CH2:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[N:9]([CH:15]=[O:17])[CH2:8][C:7]1([CH2:20][CH2:19][CH2:18]1)[CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69060228HCID 69060228, compound

Product 1

HCID 86605500HCID 86605500, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-yl)ethanone (100 mg) was dissolved in dichloromethane (2 mL), to which solution was added BBr3 (19.3 mL) at 10° C. After 1.5 h, it was quenched with water, extracted with dichloromethane, and the organic layers were washed with brine, dried and evaporated to give an oil. Elution on a column (dichloromethane:methanol=10:0.2) gave 6′-hydroxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-carbaldehyde (70 mg) as a white solid.

Workup

  1. customit was quenched with water
  2. extractionextracted with dichloromethane
  3. washthe organic layers were washed with brine
  4. customdried
  5. customevaporated
  6. customto give an oil
  7. washElution on a column (dichloromethane:methanol=10:0.2)

Sources & evidence

ORD record
ord-a95a14bbf34647c9bb46b3d845b8ac3c
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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