Bromine → HCID 18739878, compound

HRID 1934890Notes

Reaction equation

HRID 1934890 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C@H:15]4[CH2:16][C@H:12]([CH2:13][CH2:14]4)[C@H:11]3[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Br:22]Br>C(O)(=O)C.C(Cl)Cl.C(=O)([O-])O>[Br:22][C:3]1[C:4]2[CH:9]=[C:8]([C@H:10]3[C@H:15]4[CH2:16][C@H:12]([CH2:13][CH2:14]4)[C@H:11]3[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 18739873HCID 18739873, compound

Product 1

HCID 18739878HCID 18739878, compoundYield 97.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 769Bicarbonate IonSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,2R,3S,4R)-3-(1-benzothien-5-yl)-N,N-dimethylbicyclo[2,2,1]heptane-2-carboxamide (30 mg, 0.1 mmol) in acetic acid (2 mL) was added bromine (5.5 μL, 0.1 mmol) and the mixture was stirred at room temperature for 16 hours. The mixture was diluted with methylene chloride (5 mL) and neutralised by careful addition of a saturated hydrogen carbonate solution. The layers were separated and the aqueous was extracted with methylene chloride (2×5 mL). The organic extracts were washed with water, dried over magnesium sulfate and evaporated in vacuo to give (1S,2R,3S,4R)-3-(3-bromo-1-benzothien-5-yl)-N,N-dimethylbicyclo[2,2,1]heptane-2-carboxamide as a glass (37 mg, 97%). M/e 378/380 (MH+).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with methylene chloride (2×5 mL)
  3. washThe organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c185260212794abb82d1b68c7a8e0510
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

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