Triethylamine → HCID 89751830, compound

HRID 1521807Notes

Reaction equation

HRID 1521807 reaction equation
[CH:1]1[C:13]2[C:12]3[CH:14]=[CH:15][C:16]([C:18](=[O:22])[CH:19](Br)[Br:20])=[CH:17][C:11]=3[O:10][CH2:9][CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[C:3]([C:23](=[O:27])[CH:24](Br)[Br:25])[CH:2]=1.CCN(CC)CC.P([O-])(OCC)OCC>C1COCC1>[CH:1]1[C:13]2[C:12]3[CH:14]=[CH:15][C:16]([C:18](=[O:22])[CH2:19][Br:20])=[CH:17][C:11]=3[O:10][CH2:9][CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[C:3]([C:23](=[O:27])[CH2:24][Br:25])[CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 89751862HCID 89751862, compound

Product 1

HCID 89751830HCID 89751830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1′-(7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonine-3,11-diyl)bis(2,2-dibromoethanone) (1b) (0.38 g, 0.61 mmol) in THF (7 mL) at 0° C. was added Et3N (0.09 mL, 0.61 mmol) and diethyl phosphite (0.24 mL, 1.82 mmol). The reaction mixture was gradually warmed to room temperature, stirred for 1 h and concentrated under reduced pressure. The residual contents were partitioned between EtOAc and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to yield an yellow oil (1c) which was used in the next step without further purification (0.15 g, 53%). m/z 468.9 (M+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residual contents were partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ecdcbef2dbe4b6ca4a2b271ebf585a2
Source dataset
uspto-grants-2015_07
Patent number
US09073943B2

Reaction notes

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