Boron tribromide dichloromethane → HCID 68862057, compound

HRID 898873Notes

Reaction equation

HRID 898873 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:12]1[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]1=[O:22])[CH2:6]2.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:12]1[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]1=[O:22])[CH2:6]2

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 68860699HCID 68860699, compound

Product 1

HCID 68862057HCID 68862057, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To 2-(5-methoxyindan-2-yl)isoindole-1,3-dione (19.7 g; 67 mmol) dissolved in anhydrous CH2Cl2 (350 mL) and cooled to −60° C., is added a 1.0 M solution of boron tribromide-CH2Cl2 (340 mL), dropwise at a rate to maintain the internal temperature between −50 and −60° C. The reaction mixture is allowed to warm to RT and stirred for an additional 5 h. The reaction is cooled to 0° C., quenched with saturated NaHCO3 (500 mL) and stirred for an additional 0.5 h at RT. The precipitate is filtered, washed with H2O, suspended in ether, filtered and dried under vacuo to afford 14.8 g (79%) of 2-(5-hydroxyindan-2-yl)isoindole-1,3-dione as a beige solid.

Workup

  1. temperaturedropwise at a rate to maintain the internal temperature between −50 and −60° C
  2. temperatureto warm to RT
  3. temperatureThe reaction is cooled to 0° C.
  4. customquenched with saturated NaHCO3 (500 mL)
  5. stirringstirred for an additional 0.5 h at RT
  6. filtrationThe precipitate is filtered
  7. washwashed with H2O
  8. filtrationfiltered
  9. customdried under vacuo

Sources & evidence

ORD record
ord-16fabb4e9c5144de97bf1a14fed70a08
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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