Water → HCID 22152293, compound

HRID 1111332Notes

Reaction equation

HRID 1111332 reaction equation
[CH3:1][C:2]1([CH3:14])[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.[Br:15]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:15][C:6]1[C:7]([OH:13])=[C:8]([CH:11]=[O:12])[CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2([CH3:14])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22152290HCID 22152290, compound

Product 1

HCID 22152293HCID 22152293, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.1 g (16.3 mmol) 1,1-dimethyl-5-hydroxyindan-6-carboxaldehyde and 3.1 g (17.4 mmol) of N-bromosuccinimide in 50 ml of methylene chloride was stirred at ambient temperature for 2 days. Water (50 ml) was added. The organic phase was dried and evaporated. The residue was filtered through silica gel (20 g) using a gradient from hexane to 2:98 (v/v) ether:hexane as eluent. There was obtained 4.0 g (14.8 mmol, 91%) of 4-bromo-1,1-dimethyl-5-hydroxyindan-6-carboxaldehyde as yellow crystals after crystallization from ethanol; mp 77.5°-78.5° C.

Workup

  1. customThe organic phase was dried
  2. customevaporated
  3. filtrationThe residue was filtered through silica gel (20 g)

Sources & evidence

ORD record
ord-34389ed3945b485bb2aca9ba04667c60
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

Loading…