Boron tribromide → HCID 56950692, compound

HRID 1518927Notes

Reaction equation

HRID 1518927 reaction equation
[F:1][C:2]1[C:3]([CH3:19])=[C:4]([C:14]([O:17]C)=[CH:15][CH:16]=1)[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3]([CH3:19])=[C:4]([C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 56950691HCID 56950691, compound

Product 1

HCID 56950692HCID 56950692, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 30 L 4-neck flask equipped with mechanical stirrer, thermometer and gas inlet was charged with a solution of compound 62 (1140 g, 4.38 mol) in CH2Cl2 (15 L). The brown solution was cooled to −78° C. with dry ice acetone bath under small N2 flow. A solution of BBr3 in CH2Cl2 (4.5 L, 5.26 mol) was added to the reaction at −70˜−78° C. with stirring over 74 min. The reaction mixture was the allowed to warm to 20˜25° C. over 3 h and stirred at room temperature for 16 h. Saturated aqueous NaHCO3 was added to the reaction mixture slowly to pH 2˜3. After stirring for 5 min, the layers were separated and the aqueous layer was extracted with CH2Cl2 (2×1 L). The organic layers were combined and washed with brine (2×2 L). The organic layer was dried over Na2SO4 and filtered and the filtrate was concentrated under reduced pressure to give 1100 g (>100%) of crude compound 63 as brown oil: 1H NMR (400 MHz, CDCl3) δ 10.66 (s, 1H), 7.50-7.44 (m, 2H), 7.36-7.31 (m, 1H), 7.26-7.18 (m, 3H), 6.86 (dd, J=9.3, 4.9 Hz, 1H), 2.60 (d, J=2.4 Hz, 3H); MS (ESI) m/z 245.11 (M−H).

Workup

  1. customA 30 L 4-neck flask equipped with mechanical stirrer
  2. temperatureto warm to 20˜25° C. over 3 h
  3. stirringstirred at room temperature for 16 h
  4. stirringAfter stirring for 5 min
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted with CH2Cl2 (2×1 L)
  7. washwashed with brine (2×2 L)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ae791bfc3f4eeebcff420146e8e1be
Source dataset
uspto-grants-2015_07
Patent number
US09073829B2

Reaction notes

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