Boron tribromide → HCID 22219609, compound

HRID 1013096Notes

Reaction equation

HRID 1013096 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:17]2[CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[C:17]2[CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])[CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22219597HCID 22219597, compound

Product 1

HCID 22219609HCID 22219609, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 M solution of BBr3 (1.1 L, 1.6 equiv.), cooled at 0° C. with an ice water bath, add 6-methoxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (187 g, 0.684 mol) in DCM (200 mL) over 1 hr, while maintaining the temperature between 0° C. and 10° C. Warm the reaction mixture to RT and stir until HPLC indicates completion of the reaction (about 2 h.). Cool the solution to 0° C. and transfer it via cannula into an ice water solution (1.2 L), thereby precipitating the product as a white solid. Add EtOAc (2 L) to dissolve most of the precipitate, separate the layers and concentrate the organic layer. Extract the aqueous layer three times with EtOAc (2×2 L, 1×1 L). Wash the combined organic layers with water (2 L), and then brine (2 L), dry (sodium sulfate) and concentrate to give the title compound as a light yellow solid (166.3 g, 94%). Use the product for the next step without further purification. Prepare an analytical sample utilizing silica gel chromatography, eluting with 40:60 diethyl ether:hexanes.

Workup

  1. temperaturewhile maintaining the temperature between 0° C. and 10° C
  2. customcompletion of the reaction (about 2 h.)
  3. temperatureCool the solution to 0° C.
  4. customprecipitating the product as a white solid
  5. dissolutionAdd EtOAc (2 L) to dissolve most of the precipitate
  6. customseparate the layers
  7. concentrationconcentrate the organic layer
  8. extractionExtract the aqueous layer three times with EtOAc (2×2 L, 1×1 L)
  9. washWash the combined organic layers with water (2 L)
  10. dry with materialbrine (2 L), dry (sodium sulfate)
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-9885912b0abf4054847f9489644393bb
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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