Hydrochloric Acid → HCID 53359012, compound

HRID 410016Notes

Reaction equation

HRID 410016 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:34])[C:8]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)=[C:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=3)[S:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:9]2[S:10][C:11]3[C:6]([C:7](=[O:34])[C:8]=2[C:24]2[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=3)=[CH:19][CH:18]=1)([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 67365285HCID 67365285, compound

Product 1

HCID 53359012HCID 53359012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(7-methoxy-2-(4-(methoxycarbonyl)benzyl)-4-oxo-4H-thiochromen-3-yl)benzoate (105 mg, 0.23 mmol) in dry DCM (3 ml) was added BBr3 (0.2 ml, 2.23 mmol) at 0° C. with stirring. The mixture was stirred at room temperature for 40 hours and poured into 1 N icy HCl solution (1 ml) with stirring. The volatiles were evaporated and the residue was purified by prep-TLC (PE:EtOAc=1:1) to afford the desired product in Example 7 as a pink solid (15 mg, 16%).

Workup

  1. stirringThe mixture was stirred at room temperature for 40 hours
  2. stirringwith stirring
  3. customThe volatiles were evaporated
  4. customthe residue was purified by prep-TLC (PE:EtOAc=1:1)

Sources & evidence

ORD record
ord-8e49f439d3094075a304c310dad4a34b
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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