Boron tribromide → HCID 118013407, compound

HRID 1049620Notes

Reaction equation

HRID 1049620 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8](/[CH:21]=[CH:22]/[C:23]#[N:24])[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8](/[CH:21]=[CH:22]/[C:23]#[N:24])[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118005978HCID 118005978, compound

Product 1

HCID 118013407HCID 118013407, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (9.0 mmol, 1M in CH2Cl2) was added dropwise to a solution of 10 (1.8 mmol) in dry CH2Cl2 (4.0 mL) under N2 at −78° C. The reaction mixture was stirred at this temperature for 1 h. After this period, the reaction was allowed to warm to room temperature and stirred for 12 h. After reaction completion, the solution was quenched with methanol, and concentrated in vacuo. The residue was extracted with CH2Cl2 and washed with a solution of NaHCO3. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give (E)-3-(3-chloro-5-(2-hydroxyphenoxy)phenyl)acrylonitrile (11) (0.14 g, 51%) 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1H), 7.21-7.10 (m, 2H), 7.11-7.01 (m, 2H), 6.92 (ddt, J=16.0, 14.5, 4.9 Hz, 3H), 5.85 (dd, J=16.6, 5.2 Hz, 1H), 5.51 (s, 1H).

Workup

  1. waitAfter this period
  2. stirringstirred for 12 h
  3. customAfter reaction completion
  4. customthe solution was quenched with methanol
  5. concentrationconcentrated in vacuo
  6. extractionThe residue was extracted with CH2Cl2
  7. washwashed with a solution of NaHCO3
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated by rotary evaporation
  11. custompurified by column chromatography

Sources & evidence

ORD record
ord-4206ef81b5324a379f913d15d3254e63
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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