Hydrochloric Acid → HCID 85885812, compound

HRID 388288Notes

Reaction equation

HRID 388288 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:3]=1[O:4][CH2:5][C:6]([NH2:8])=O.B.CSC.[ClH:18]>O1CCCC1>[ClH:18].[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:3]=1[O:4][CH2:5][CH2:6][NH2:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 22557231HCID 22557231, compound

Product 1

HCID 85885812HCID 85885812, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,6-dibromo-phenoxy)acetamide (9.3 g, 0.03 mol) in tetrahydrofuran (100 mL) was heated to reflux and borane-dimethylsulfide (4.5 mL, 0.045 mL) was added in drops over a period of 15 min. After 3 h, 20 mL of ethanolic hydrogen chloride (2M, 0.4 mol) was added. The solution was refluxed for 30 min. Upon cooling to ambient temperature a white solid precipitated which was filtered and washed with diethyl ether (20 mL) to give 2-(2,6-dibromo-phenoxy)ethylamine, hydrochloride salt (7.25 g, 73.3%). MS: MH+=294. M.p. 249.7-252.3° C.

Workup

  1. temperatureto reflux
  2. temperatureThe solution was refluxed for 30 min
  3. customprecipitated which
  4. filtrationwas filtered
  5. washwashed with diethyl ether (20 mL)

Sources & evidence

ORD record
ord-d35a0e50c094411081882b519c860e12
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

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