HCID 10106471, compound → 7-Methoxybenzo[b]thiophene

HRID 1822949Notes

Reaction equation

HRID 1822949 reaction equation
C(O[CH:4](OCC)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])C>ClC1C=CC=CC=1>[CH3:14][O:13][C:8]1[C:7]2[S:6][CH:5]=[CH:4][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 10106471HCID 10106471, compound

Product 1

HCID 110842177-Methoxybenzo[b]thiopheneYield 75.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
155 °C

Procedure

A solution of 1-[(2,2-diethoxyethyl)thio]-2-methoxybenzene (18 g, 70.3 mmol) in dry chlorobenzene (100 mL) was added slowly to a stirred solution of polyphosphoric acid (50 g) in dry chlorobenzene (300 mL) at 145° C. After addition was complete the resulting black solution was stirred at 155° C. for a further 18 hrs. After this time the reaction was allowed to cool to room temperature before being filtered through a pad of CELITE™, the solid cake was washed with dichloromethane (200 mL) and the combined organic extracts were concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane:ethyl acetate [95:5] to give a pale yellow oil (8.7 g, 75%); δH (300 MHz, CDCl3) 7.45–7.29 (4H, m, Ar), 6.75 (1H, d, Ar), 4.00 (3H, s, OCH3).

Workup

  1. additionAfter addition
  2. temperatureto cool to room temperature
  3. filtrationbefore being filtered through a pad of CELITE™
  4. washthe solid cake was washed with dichloromethane (200 mL)
  5. concentrationthe combined organic extracts were concentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-4bc637b3736b46a7a20a4301022ff21b
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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