Boron tribromide dichloromethane → HCID 68861328, compound

HRID 898865Notes

Reaction equation

HRID 898865 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([N:13]1[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]1=[O:23])[CH2:7][CH2:6]2.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([N:13]1[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]1=[O:23])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 68860277HCID 68860277, compound

Product 1

HCID 68861328HCID 68861328, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)isoindole-1,3-dione (29 g; 94.3 mmol) dissolved in anhydrous CH2Cl2 (500 mL), cooled to −60° C., is added a 1.0 M solution of boron tribromide-CH2Cl2 (471 mL), dropwise to maintain reaction temperature between −50 to −60° C. Upon completion of the addition, the reaction mixture is allowed to warm to RT and stirred for an additional 4 h. The reaction is cooled to 0° C., quenched with saturated NaHCO3 (400 mL) and stirred for an additional 0.5 h at RT. The precipitate is filtered, washed thoroughly with H2O, suspended in ether, filtered and dried under vacuo to afford 25.4 g (92%) of 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)isoindole-1,3-dione as an off-white solid.

Workup

  1. temperaturedropwise to maintain
  2. customreaction temperature between −50 to −60° C
  3. additionUpon completion of the addition
  4. temperatureto warm to RT
  5. temperatureThe reaction is cooled to 0° C.
  6. customquenched with saturated NaHCO3 (400 mL)
  7. stirringstirred for an additional 0.5 h at RT
  8. filtrationThe precipitate is filtered
  9. washwashed thoroughly with H2O
  10. filtrationfiltered
  11. customdried under vacuo

Sources & evidence

ORD record
ord-d3b4e50f86784e5883c150b0546517b9
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

Loading…