Iodine → HCID 87582968, compound

HRID 1782607Notes

Reaction equation

HRID 1782607 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH3:11].[Li+].CC([N-]C(C)C)C.[I:20]I>C1COCC1.C(OCC)(=O)C>[F:8][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([O:10][CH3:11])=[C:2]([F:1])[C:7]=1[I:20]

Participants

6

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 450736371,5-Difluoro-2-methoxy-3-methylbenzene

Product 1

HCID 87582968HCID 87582968, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,5-difluoro-2-methoxy-3-methylbenzene (0.65 g, 4.1 mmol) in THF (1 mL) was added to LDA (4.3 mmol) in THF (10 mL) at −55° C. and the solution stirred for 45 minutes. Solid iodine (1.15 g, 4.5 mmol) was added and the solution allowed to warm to ambient temperature. The solution was diluted with ethyl acetate and washed with sodium bicarbonate (saturated solution 15 mL) and sodium thiosulfate (saturated solution, 15 mL), dried (sodium sulfate) and concentrated. The residue was purified by chromatography (hexanes) to give 1,3-difluoro-2-iodo-4-methoxy-5-methylbenzene: 1H NMR (300 MHz, CDCl3): δ 6.72 (dd, 1H), 3.84 (d, 3H,), 2.26 (s, 3H).

Workup

  1. washwashed with sodium bicarbonate (saturated solution 15 mL) and sodium thiosulfate (saturated solution, 15 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (hexanes)

Sources & evidence

ORD record
ord-528c49f2164343678e241c928b704ab5
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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