Hydrochloric Acid → HCID 53357168, compound

HRID 714500Notes

Reaction equation

HRID 714500 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[C:9]([CH3:13])[S:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[C:9]([CH3:13])[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 67366890HCID 67366890, compound

Product 1

HCID 53357168HCID 53357168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(7-methoxy-2-methyl-4-oxo-4H-thiochromen-3-yl)benzoate (200 mg, 0.588 mmol) in DCM (10 ml) was added BBr3 (0.83 ml, 8.813 mmol) at room temperature and stirred for 20 hours. The mixture was poured into icy 1 N HCl (50 ml) with stirring and the precipitate was collected by filtration to obtain crude product, which was purified by prep-HPLC to afford the desired product in Example 8 as a yellow solid (57.3 mg, 31%).

Workup

  1. stirringwith stirring
  2. filtrationthe precipitate was collected by filtration
  3. customto obtain crude product, which
  4. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-4fdd1cd0f56f4cb580d2c911d7779393
Source dataset
uspto-grants-2015_11
Patent number
US09187447B2

Reaction notes

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