Methanol → HCID 21182936, compound

HRID 1386978Notes

Reaction equation

HRID 1386978 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[C:13]3[CH:28]=[CH:27][CH:26]=[CH:25][C:14]=3[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.CO>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[C:13]3[CH:28]=[CH:27][CH:26]=[CH:25][C:14]=3[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 21182793HCID 21182793, compound

Product 1

HCID 21182936HCID 21182936, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of 700 mg (1.80 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 3-methyl-4-methoxyphenyl ketone (Part B) in 25 mL of CH2Cl2 was treated with 7.2 mL of BBr3 (1.0 M in CH2Cl2). The reaction was stirred at 0° C. for 6 h, then cooled to −78° C., and was treated carefully with 50 mL of MeOH. The mixture was allowed to warm to room temperature over 1.5 h, and the volatiles were evaporated in vacuo. The dark red residue (monomethyl ether) was taken up in 75 mL dichloroethane and was treated with AlCl3 and ethanethiol according to the conditions of Example 1, Part D to afford 675 mg of an oil. Purification by radial chromatography (SiO2; gradient of 20-30% EtOAc in hexanes) afforded 410 mg (1.14 mmol; 63%) of the title compound as an orange solid.

Workup

  1. temperaturecooled to −78° C.
  2. temperatureto warm to room temperature over 1.5 h
  3. customthe volatiles were evaporated in vacuo
  4. additionwas treated with AlCl3 and ethanethiol according to the conditions of Example 1, Part D

Sources & evidence

ORD record
ord-b27842d326dd421998c286918d572be0
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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