Xanthene → HCID 86662011, compound

HRID 1464917Notes

Reaction equation

HRID 1464917 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH:6]1[C:19]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH:6]1[C:19]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:3](=[O:4])[CH2:2][Br:1])[CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][C:7]=1[C:3](=[O:4])[CH2:2][Br:1]

Participants

5

Reactant 3

HCID 7107XantheneHCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86662011HCID 86662011, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to Scheme 5, bromoacetyl chloride (4.59 ml, 54.9 mmol) was added dropwise to a solution of 9H-xanthene (5 g, 27.4 mmol) and AlCl3 (8.05 g, 60.4 mmol), DCM (100 mL) at 0° C. The reaction mixture was allowed to warm up to rt and left to stir for 72 hrs. The reaction mixture was poured onto ice (400 mL), extracted with DCM (2×200 mL). The combined organic phase was washed with brine (400 mL), dried over MgSO4, filtered and evaporated to dryness. The crude material was precipitated in EtOAc and filtered to give 1,1′-(9H-xanthene-2,7-diyl)bis(2-bromoethanone) (5-2) as a white solid (4.27 g, 36.7% yield). LC-MS (ESI): m/z 425.9 [M+H]+.

Workup

  1. waitleft
  2. additionThe reaction mixture was poured onto ice (400 mL)
  3. extractionextracted with DCM (2×200 mL)
  4. washThe combined organic phase was washed with brine (400 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude material was precipitated in EtOAc
  9. filtrationfiltered

Sources & evidence

ORD record
ord-13a9e5f2e6b74446968f9568ef90556a
Source dataset
uspto-grants-2015_04
Patent number
US08999967B2

Reaction notes

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