Iodine → HCID 89613883, compound

HRID 1473668Notes

Reaction equation

HRID 1473668 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.[I:33]I.O>CC#N>[F:1][C:2]1[CH:9]=[C:8]([I:33])[C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 2724933SelectfluorHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 89613883HCID 89613883, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-fluoro-5-methoxybenzaldehyde (Oakwood, 6.000 g, 38.9 mmol) and Selectfluor (13.79 g, 38.9 mmol) in 40 mL MeCN was treated with iodine (10.87 g, 42.8 mmol) and was heated to 80° C. for one hour. LC/MS showed mostly product, so the reaction mixture was poured into water and was extracted with DCM. The organic were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0-20% EtOAc/heptane) gave 2-fluoro-4-iodo-5-methoxybenzaldehyde (8.92 g, 31.9 mmol, 82% yield) as a 3:1 mixture with starting material. (M+H)+=281.0.

Workup

  1. extractionwas extracted with DCM
  2. dry with materialThe organic were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography (0-20% EtOAc/heptane)

Sources & evidence

ORD record
ord-9b0b379d67414e69a724d04bad652768
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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