Triethylamine → HCID 58079229, compound

HRID 2090546Notes

Reaction equation

HRID 2090546 reaction equation
[Br:1][CH:2](Br)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:22])[CH:19](Br)[Br:20])=[CH:14][CH:13]=2)[CH:6]=1)=[O:4].C(N(CC)CC)C.P([O-])(OCC)OCC>O1CCCC1>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:22])[CH2:19][Br:20])=[CH:14][CH:13]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 58079226HCID 58079226, compound

Product 1

HCID 58079229HCID 58079229, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2-dibromo-1-(3-(4-(2,2-dibromoacetyl)phenoxy)phenyl)ethanone (16 g, 28 mmol) in tetrahydrofuran (300 mL) at 0° C. was added triethylamine (3.6 mL) and diethyl phosphite (10.7 mL, 83.2 mmol). The reaction was warmed gradually to room temperature and the mixture was stirred during 30 minutes and concentrated under reduced pressure. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resultant crude material was purified by flash chromatography (silica gel: EtOAc/heptane: 3/7) to afford 2-bromo-1-(3-(4-(2-bromoacetyl)phenoxy)phenyl)ethanone (10.2 g, 88%) as yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant crude material was purified by flash chromatography (silica gel: EtOAc/heptane: 3/7)

Sources & evidence

ORD record
ord-f208d427a98542c88a425d67e2b540a9
Source dataset
uspto-grants-2013_05
Patent number
US08436036B2

Reaction notes

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