Boron tribromide → HCID 22152284, compound

HRID 2171734Notes

Reaction equation

HRID 2171734 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:13]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:11])[CH3:12])=[CH:4][C:3]=1[OH:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67053816HCID 67053816, compound

Product 1

HCID 22152284HCID 22152284, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-bromo-5-methoxy-1,1-dimethyl-indan (0.6 g, 2.35 mmol) in CH2Cl2 (30 mL) was added BBr3 (1M in CH2Cl2, 4.70 mmol) dropwise at −78° C. Following addition the mixture was allowed to warm to room temperature and subsequently stirred at room temperature for 2 h. The reaction mixture was then quenched with MeOH (5 mL). Aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/heptane) provided 0.51 g (90%) of 6-bromo-1,1-dimethyl-indan-5-ol.

Workup

  1. additionaddition the mixture
  2. customThe reaction mixture was then quenched with MeOH (5 mL)
  3. additionAqueous sodium hydrogen carbonate (10 mL) was added
  4. stirringThe reaction mixture was stirred at room temperature for 1 hour
  5. extractionThe reaction mixture was extracted with CH2Cl2
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ec845f5e6a9f4fa6afcb9e8deca0b9e4
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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