Iodine → HCID 20086443, compound

HRID 2379764Notes

Reaction equation

HRID 2379764 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>O1CCCC1>[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 mmmol) 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 dark red solution for one minute, iodine (8.64 g; 34.08 mmol) was added as a tetrahydrofuran (THF) solution (50 ml). The reaction mixture was stirred for 30 minutes at -78° C. and one hour at room temperature (about 24° C.). The reaction 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): 2.79 (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 (about 24° C.)
  2. customThe reaction 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-37604dec0ad448ed94c1c476bf152f85
Source dataset
uspto-grants-1994_11
Patent number
US05364876

Reaction notes

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