Boron tribromide → HCID 21966485, compound

HRID 2212598Notes

Reaction equation

HRID 2212598 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-6fcdd6661e6540feb76b3b229da6379a
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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