Water → HCID 20816513, compound

HRID 1399907Notes

Reaction equation

HRID 1399907 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O>C(Cl)Cl>[N:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 4189043HCID 4189043, compound

Product 1

HCID 20816513HCID 20816513, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-(3-methoxyphenyl)quinoline (900 mg, 3.83 mmol) in CH2Cl2 (50 ml) was added BBr3 (2.4 g, 14 mmol) at 0° C. The mixture was stirred for 2 h at 0° C. then until the reaction was completed. The mixture was added drop wise to iced water (50 mL), and then extracted with CH2Cl2 (2×20 mL). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated to give a yellow solid which was used in next step without further purification. (720 mg, Yield 85%). LCMS (m/z): 222.1 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (2×20 mL)
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a yellow solid which
  6. customwas used in next step without further purification

Sources & evidence

ORD record
ord-2862822dd8b04ccf9f2be2037ec6397e
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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