Iodine → 6-Fluoro-7-iodo-3-propylchroman

HRID 2420635Notes

Reaction equation

HRID 2420635 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][O:9]2)=[CH:4][C:3]=1[F:15].C([Li])CCC.[I:21]I>C1COCC1.CCCCCC>[F:15][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[I:21])[O:9][CH2:8][CH:7]([CH2:12][CH2:13][CH3:14])[CH2:6]2

Participants

6

Reactant 3

HCID 807IodineHCID 59288371HCID 59288371, compoundHCID 178418339Butyllithium

Product 1

HCID 592883606-Fluoro-7-iodo-3-propylchroman

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

10.6 g (38.8 mmol) of 7-bromo-6-fluoro-3-propylchroman are initially introduced in 100 ml of THF, and 27 ml (43.0 mmol) of a 15 percent solution of n-butyllithium in hexane are added dropwise. After 90 min, 10.0 g (39.4 mmol) of iodine, dissolved in 50 ml of THF, are added, the mixture is stirred for 1 h, and the cooling is removed. The batch is diluted with MTB ether, washed with water and with sat. sodium hydrogensulfite soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is filtered through silica gel with heptane/toluene (4:1), giving 6-fluoro-7-iodo-3-propylchroman as a colourless solid, which is sufficiently pure for further reaction.

Workup

  1. additionare added
  2. customthe cooling is removed
  3. additionThe batch is diluted with MTB ether
  4. washwashed with water and with sat. sodium hydrogensulfite soln
  5. dry with materialand dried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. filtrationthe crude product is filtered through silica gel with heptane/toluene (4:1)

Sources & evidence

ORD record
ord-13e0360e8d5845d5a206004326512946
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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