Boron tribromide → HCID 15983357, compound

HRID 1881238Notes

Reaction equation

HRID 1881238 reaction equation
[Cl:1][C:2]1[C:3]2[CH:18]=[C:17]([O:19]C)[C:16]([O:21]C)=[C:15]([C:23]#[N:24])[C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:3]2[CH:18]=[C:17]([OH:19])[C:16]([OH:21])=[C:15]([C:23]#[N:24])[C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67094206HCID 67094206, compound

Product 1

HCID 15983357HCID 15983357, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

(3-Chloro-7-cyano-5,6-dimethoxy-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone (0.05 g) was suspended in dichloromethane under nitrogen, cooled to −20° C. and treated dropwise with a solution of 1M boron tribromide in dichloromethane. The suspension was stirred at −20° C. for 30 minutes and in cool overnight. The mixture was poured into ice-cold water and stirred at room temperature for 30 minutes. The product was filtered and purified by a preparative plate (reverse phase) using a mixture of toluene, ethyl acetate and acetic acid (8:1:1) as an eluent.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. stirringstirred at room temperature for 30 minutes
  3. filtrationThe product was filtered
  4. custompurified by a preparative plate (reverse phase)
  5. additiona mixture of toluene, ethyl acetate and acetic acid (8:1:1) as an eluent

Sources & evidence

ORD record
ord-7c1b323a578f4a58a0a98f74a20552d0
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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