Isopropyl iodide → HCID 86695615, compound

HRID 594270Notes

Reaction equation

HRID 594270 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].I[CH:12]([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOCC>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:12]([CH3:14])[CH3:13])[C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 27373276-Fluorosalicylaldehyde

Product 1

HCID 86695615HCID 86695615, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of commercially available 2-fluoro-6-hydroxybenzaldehyde (3.000 g; 21.40 mmol), 2-iodopropane (10.919 g; 64.20 mmol), K2CO3 (5.918 g; 42.80 mmol), and Cs2CO3 (1.395 g; 4.28 mmol) in anh. DMF (63 ml) was stirred at rt, under nitrogen, for 16 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-fluoro-6-isopropoxybenzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.74 min.; [M+H]+: 183.15 g/mol.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-71efddc98ecd4bc19242c58fbdebbae5
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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