Water → HCID 68654780, compound

HRID 229262Notes

Reaction equation

HRID 229262 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68654763HCID 68654763, compound

Product 1

HCID 68654780HCID 68654780, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (5° C.) solution of {(4-bromophenyl)[3-(methyloxy)phenyl]methylidene}cycloheptane (192) (0.557 g, 1.5 mmol) in CH2Cl2 (50 mL) was added BBr3 (0.425 mL, 4.5 mmol) slowly. The reaction mixture was stirred between 5° C. and 20° C. for 4 h and then carefully poured into water (100 mL). The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×50 mL) and the combined organic layer dried (Na2SO4). Concentration and purification by flash column chromatography gave 0.44 g (82%) of compound 193 as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.41 (d, J=8.4 Hz, 2H), 7.17 (dd, J1=7.8 Hz, J2=7.8 Hz, 1H), 7.05 (d, J=8.4 Hz, 2H), 6.74 (br d, J=7.5 Hz, 1H), 6.69 and 6.67 (dd, J1=2.4 Hz, J2=8.1 Hz, 1H), 6.62 (app t, J=1.8 Hz), 4.71 (s, 1H), 2.32 (br, m, 4H), 1.59 (br s, 8H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with CH2Cl2 (2×50 mL)
  3. dry with materialthe combined organic layer dried (Na2SO4)
  4. concentrationConcentration and purification by flash column chromatography

Sources & evidence

ORD record
ord-2f8d9390255f481f9cc108c7cb954c4b
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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