Boron tribromide → HCID 11311098, compound

HRID 1602123Notes

Reaction equation

HRID 1602123 reaction equation
B(Br)(Br)[Br:2].CO[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])[O:16][CH3:17].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Br:2][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])[O:16][CH3:17]

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21191815HCID 21191815, compound

Product 1

HCID 11311098HCID 11311098, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

38.6 g (150 mmol) of boron tribromide are added dropwise to 10 g (51 mmol) of methyl N-(2-methoxymethylphenyl)-carbamate (Example 2b) in 100 ml of methylene chloride. Stirring is carried out for 2 hours, after which the vigorously stirred reaction mixture is added dropwise to a solution of 11.8 g (0.17 mol) of NaHCO3 in water. The organic phase is separated off and the aqueous phase is extracted once with methylene chloride and once with ethyl acetate. The combined organic phases are dried over MgSO4 and evaporated down. 9.5 g (39 mmol=76%) of the title compound are obtained as a colorless solid. mp.=132° C.

Workup

  1. customafter which the vigorously stirred reaction mixture
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted once with methylene chloride and once with ethyl acetate
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customevaporated down

Sources & evidence

ORD record
ord-294d09720eb8499f9f7673dbbc466f5f
Source dataset
uspto-grants-1999_11
Patent number
US05981532

Reaction notes

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