Water → 2-Acetyl-2-(tert-butoxycarbonyl)-5-fluoro-indane

HRID 1045087Notes

Reaction equation

HRID 1045087 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10]Br.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=[O:21].O>CC(CC)=O>[C:20]([C:19]1([C:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C:4]2[C:3](=[CH:8][CH:7]=[C:6]([F:9])[CH:5]=2)[CH2:2]1)(=[O:21])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15538Tert-butyl acetoacetateHCID 117809721,2-Bis(bromomethyl)-4-fluorobenzene

Product 1

HCID 509065702-Acetyl-2-(tert-butoxycarbonyl)-5-fluoro-indane

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 10 g of 1,2-bis-(bromomethyl)-4-fluoro-benzene in 200 ml of methylethylketone were added 29.4 g of potassium carbonate followed by 6.7 g of tert-butyl acetoacetate. The mixture was stirred for 16 h at ambient temperature. 200 ml of water were added. The phases were separated and the aqueous phase was extracted once with 100 ml of methylethylketone. The combined organic phases were washed once with 100 ml of water. The solvent was evaporated and to the resulting oil were added 20 ml of methanol. After 1 h stirring at ambient temperature the product was filtered off, washed with 2×5 ml of methanol and dried. Yield: 6.2 g. Melt.p. 73° C. 1HNMR: δ=1.48 ppm (s, 9H); 2.25 ppm (s, 3H); 3.44 ppm (AB, 2H); 3.47 (AB, 2H); 6.87 ppm (m, 2H); 7.12 ppm (dd, 1H)

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted once with 100 ml of methylethylketone
  3. washThe combined organic phases were washed once with 100 ml of water
  4. customThe solvent was evaporated and to the resulting oil
  5. additionwere added 20 ml of methanol
  6. stirringAfter 1 h stirring at ambient temperature the product
  7. filtrationwas filtered off
  8. washwashed with 2×5 ml of methanol
  9. customdried
  10. custom73° C

Sources & evidence

ORD record
ord-69207b55e0144c6ba08f7ec631c066e5
Source dataset
uspto-grants-2013_10
Patent number
US08563766B2

Reaction notes

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