Iodine → HCID 20086443, compound

HRID 1608498Notes

Reaction equation

HRID 1608498 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][O:8][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[I:17]I>C1COCC1>[I:17][C:4]1[CH:3]=[CH:2][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][O:8][CH2:9]2

Participants

5

Reactant 3

HCID 807IodineHCID 105605257-bromoisochromanHCID 178418306HCID 178418306, compound

Product 1

HCID 20086443HCID 20086443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7-bromoisochroman (6.6 g; 30.98 mmol) in THF (100 ml) was cooled to -78° C. and treated with 2.1 eq of tert-butyllithium (40 ml of a 1.7M solution). After stirring the solution for one minute, iodine (8.64 g; 34.08 mmol) was added as a THF solution (50 ml). The reaction mixture was stirred for 30 minutes at -78° C. and one hour at room temperature. It was quenched with saturated aqueous ammonium chloride, and the organic phase was washed with aqueous sodium thiosulfate and brine, dried, and freed of solvent. The crude product was recrystallized from hexane to provide the pure 5-iodoisochroman as a white crystalline solid, mp= 54°-56° C. (4.1 g; 51%). 1H NMR (CDCl3): δ2.79 (t, 2H); 3.94 (t, 2H); 4.70 (s, 2H); 6.85 (d, 1H); 7.32 (s, 1H); 7.46 (d, 1H). IR (nujol): 2931, 2852, 1550, 1252, 1190, 1105, 1005, 987 cm-1.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes at -78° C. and one hour at room temperature
  2. customIt was quenched with saturated aqueous ammonium chloride
  3. washthe organic phase was washed with aqueous sodium thiosulfate and brine
  4. customdried
  5. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-0b5988a505e44fe88e95811fd5087d2f
Source dataset
uspto-grants-1995_03
Patent number
US05395827

Reaction notes

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