Water → HCID 19423390, compound

HRID 743026Notes

Reaction equation

HRID 743026 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([OH:13])[CH:3]=1.[I:14]Cl.O.S([O-])([O-])=O.[Na+].[Na+]>CCCCCCC>[F:1][C:2]1[C:12]([I:14])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([OH:13])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 24640Iodine chlorideHCID 22478444Ethyl 4-fluoro-2-hydroxybenzoate

Product 1

HCID 19423390HCID 19423390, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

Ethyl 4-fluoro-2-hydroxybenzoate (10.2 g, 55 mmol)) was dissolved in n-heptane. Iodo monochloride (12 g, 74 mmol) was added dropwise at ambient temperature with stirring. After 1 h, water was added and then solid sodium sulfite in small portions until the suspension was decolourized. More n-heptane was added to clear solution and the phases separated. The organic phase was dried and concentrated. The product crystallized on cooling. It was collected by filtration and washed with cold n-heptane. The crude yield was 10 g. The product was a mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%) and the 5 chloro analogue (about 20%).

Workup

  1. customthe phases separated
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe product crystallized
  5. temperatureon cooling
  6. filtrationIt was collected by filtration
  7. washwashed with cold n-heptane
  8. additiona mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%)

Sources & evidence

ORD record
ord-392531f8a74a464590ea1cf53c4b0602
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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