Iodine → HCID 19705711, compound

HRID 727432Notes

Reaction equation

HRID 727432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.C([Li])CCC.[I:17]I>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([I:17])[S:8][C:7]=2[CH:11]=1

Participants

5

Reactant 3

HCID 807IodineHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 19705711HCID 19705711, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-methoxybenzo[b]thiophene (5.00 g, 30.49 mmol) in 200 mL of anhydrous THF at -78° C., was added n-butyllithium (20.0 mL, 32.01 mmol, 1.6M solution in hexanes). After stirring for 15 minutes, a solution of I2 (8.10 g, 32.01 mmol) in 25 mL of anhydrous THF was introduced dropwise via canula. The resulting mixture was allowed to gradually warm to ambient temperature. The reaction was quenched by distributing between ethyl acetate/brine (150 mL each). The layers were separated and the organic layer was dried over sodium sulfate. Concentration in vacuo produced a tan solid that was recrystallized from hexanes to provide 6.70 g (75%) of 6-methoxy-2-iodobenzo[b]thiophene. mp 75°-77° C. 1H NMR (CDCl3) d 7.59 (d, J=8.6 Hz, 1H), 7.42 (s, 1H), 7.22 (d, J=2.0 Hz, 1H), 6.92 (dd, J=8.6, 2.0 Hz, 1H), 3.86 (s, 3H). FD mass spec: 290. Anal. Calcd. for C9H7OSI: C, 37.26; H, 2.43. Found: C, 37.55; H, 2.43.

Workup

  1. customThe reaction was quenched
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationConcentration in vacuo
  5. customproduced a tan solid
  6. customthat was recrystallized from hexanes

Sources & evidence

ORD record
ord-e2c30347245344d497f0a00f672befcf
Source dataset
uspto-grants-1998_01
Patent number
US05712390

Reaction notes

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