Boron tribromide → HCID 22152290, compound

HRID 1111331Notes

Reaction equation

HRID 1111331 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([O:13]C)=[C:8]([CH:11]=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([OH:13])=[C:8]([CH:11]=[O:12])[CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22152297HCID 22152297, compound

Product 1

HCID 22152290HCID 22152290, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.25 g (20.8 mmol) of 1,1-dimethyl-5-methoxyindan-6-carboxaldehyde in 25 ml of methylene chloride and cooled in an ice water bath was added 22 ml (22.0 mmol, 1M in methylene chloride) of boron tribromide. After stirring for 1 h, the reaction mixture was poured into 100 ml of ice water The organic phase was dried and evaporated. The residue was chromatographed on silica gel (50 g) using hexane as eluent There was obtained 3.37 g (17.7 mmol, 85%) of 1,1-dimethyl-5-hydroxyindan-6-carboxaldehyde as a white solid; mp 40°-40.5° C.

Workup

  1. customwas dried
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (50 g)

Sources & evidence

ORD record
ord-aaf92925cf1549f3a19c1dd0a9aa3679
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

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