Boron tribromide → HCID 59730230, compound

HRID 130804Notes

Reaction equation

HRID 130804 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([O:16]C)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 17815182HCID 17815182, compound

Product 1

HCID 59730230HCID 59730230, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2,2,2-trifluoro-1-(7-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)ethanone (10.0 g, 36.6 mmol) in dichloromethane (750 mL). Add BBr3 (11.0 mL, 116 mmol) and stir for 4 hours. Quench the reaction mixture with water (350 mL). Filter the suspension, then separate the two layers. Extract the aqueous layer with dichloromethane (2×300 mL). Dry the combined organic extracts over MgSO4, filter and concentrate to give the title compound (8.62 g, 91%): MS ES+ 260 (M+H)+, ES− 258 (M−H)−; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=8.8 min, 100% purity.

Workup

  1. customQuench the reaction mixture with water (350 mL)
  2. filtrationFilter the suspension
  3. customseparate the two layers
  4. extractionExtract the aqueous layer with dichloromethane (2×300 mL)
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-fd43d87c10a446598a769c00e81690cf
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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