Boron tribromide → HCID 21966485, compound

HRID 1790201Notes

Reaction equation

HRID 1790201 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH3:19])=[C:14]([O:17]C)[CH:15]=2)[C:10]([CH3:21])([CH3:20])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH3:19])=[C:14]([OH:17])[CH:15]=2)[C:10]([CH3:20])([CH3:21])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21966476HCID 21966476, compound

Product 1

HCID 21966485HCID 21966485, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 1-benzyl-6-methoxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (1.52 g, 5.15 mmol) in anhydrous dichloromethane (50 mL) was added slowly, under argon at −78° C., BBr3 (0.87 mL, 9.27 mmol). The reaction was warmed up to −20° C. and stirred overnight at room temperature. Water and the layer separated. The aqueous layer was neutralized with NaHCO3 and extracted with dichloromethane. The organic combined extract was washed with aqueous NaHCO3, water and brine, dried over MgSO4, filtered and evaporated to give 1-benzyl-6-hydroxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (93% yield). 1H NMR (300 MHz; CDCl3): 1.38 (s, 6 H), 2.19 (s, 3 H), 4.82 (s, 2 H), 5.47 (br s, 1 H), 6.26 (s, 1 H), 6.93 (s, 1 H), 7.26 (m, 5 H).

Workup

  1. customWater and the layer separated
  2. extractionextracted with dichloromethane
  3. extractionThe organic combined extract
  4. washwas washed with aqueous NaHCO3, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-47389a4cedf14c17a95ffc3eefc86c4e
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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