Dichloromethane → HCID 19906414, compound

HRID 2371809Notes

Reaction equation

HRID 2371809 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:9]=2)[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.C(Br)(Br)(Br)Br>C(OCC)(=O)C.O1CCCC1>[F:14][C:13]([F:15])([F:16])[C:12]([NH:11][C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH:3]=[CH:2]2)=[CH:6][CH:7]=1)=[O:17]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19906362HCID 19906362, compound

Product 1

HCID 19906414HCID 19906414, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-hydroxy-6-(trifluoroacetamido)indane (4.37 g), triphenylphosphine (7.01 g), methylene chloride (70 ml) and tetrahydrofuran (7 ml), at 0° C., was added carbon tetrabromide (8.87 g) in four portions. After 15 min, the reaction mixture was allowed to warm to room temperature and stirred for 4 h. Ethyl acetate was added and the solution was washed (water, brine), dried (MgSO4) and evaporated. The residue was flashed chromatographed, eluting with methylene chloride, to give 6-(trifluoroacetamido)-3H-indene (3.09 g, 76%) as a colorless solid; mp 131.5°-132.5° C.; MS(CI), m/e=228(M+H).

Workup

  1. washthe solution was washed (water, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was flashed chromatographed
  5. washeluting with methylene chloride

Sources & evidence

ORD record
ord-62985c76edc84610af2439eefe26e463
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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