Boron tribromide → HCID 22119820, compound

HRID 1274645Notes

Reaction equation

HRID 1274645 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:28])([CH3:27])[C:22]([O:24]CC)=[O:23])[C:17]=3[CH:29]=2)[C:3]1=[O:30].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:27])([CH3:28])[C:22]([OH:24])=[O:23])[C:17]=3[CH:29]=2)[C:3]1=[O:30]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18314487HCID 18314487, compound

Product 1

HCID 22119820HCID 22119820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-α,α-dimethyl-1,2-benzisothiazole-3-acetate (6.30 g, 0.0143 mol) in methylene chloride at 0° C. is added boron tribromide in methylene chloride (1.0 M, 100 ml, 0.100 mol) such that the temperature does not exceed 15° C. The resultant mixture is stirred one hour at ambient temperature, quenched with 3 N hydrochloric acid, and diluted with methylene chloride. The organic layer is separated, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound as an off-white solid (mp 155-156° C.) which is identified by NMR and IR spectral analyses.

Workup

  1. customdoes not exceed 15° C
  2. customquenched with 3 N hydrochloric acid
  3. additiondiluted with methylene chloride
  4. customThe organic layer is separated
  5. washwashed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17166df07975465cab2acb562b0ccce3
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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