Triethylamine → 2-Bromo-1-(6-bromonaphthalen-2-yl)ethanone

HRID 1486401Notes

Reaction equation

HRID 1486401 reaction equation
[Br:1][CH:2](Br)[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=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:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 866699782,2-Dibromo-1-(6-bromonaphthalen-2-yl)ethanone

Product 1

HCID 126988982-Bromo-1-(6-bromonaphthalen-2-yl)ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-dibromo-1-(6-bromonaphthalen-2-yl)ethanone (90.0 g, 221 mmol, 1.00) was dissolved in tetrahydrofurane (800 mL), triethylamine (27.67 mL, 199 mmol, 0.9 equiv.) was added followed by diethyl phosphite (45.8 g, 332 mmol, 1.50 equiv.). The reaction mixture was stirred overnight. The reaction mixture was filtrated and the solvent was removed in vacuum. The obtained residue was dissolved in ethyl acetate (1.2 L) and washed with water. The organic layer was separated, dried over sodium sulphate, filtrated and concentrated to yield crude 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (70.3 g). Recrystallization from acetonitrile gave 30 g (first batch) and 6.5 g (second batch) of 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (50%)

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was removed in vacuum
  3. dissolutionThe obtained residue was dissolved in ethyl acetate (1.2 L)
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltrated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f8ee39b9bb664b66b4f71993f6069e75
Source dataset
uspto-grants-2016_08
Patent number
US09427428B2

Reaction notes

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