Sodium Azide → HCID 86599122, compound

HRID 2116011Notes

Reaction equation

HRID 2116011 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[C:18]([F:29])=[C:19]([F:28])[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O.C(OCC)(=O)C>[F:29][C:18]1[C:16]2[CH2:17][CH:13]([CH2:12][N:30]=[N+:31]=[N-:32])[O:14][C:15]=2[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][C:19]=1[F:28]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86599121HCID 86599121, compound

Product 1

HCID 86599122HCID 86599122, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (±)-(4,5-difluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.0 g, 2.40 mmol) in N,N-dimethylformamide (25 mL) was added sodium azide (0.781 g, 12.02 mmol) and the reaction mixture was heated to 70° C. and allowed to stir for 3 h. The reaction mixture was allowed to cool and the solvent was removed in vacuo to provide a crude solid. The residue was suspended in ethyl acetate (100 mL) and washed with water (50 mL) and aqueous sodium chloride (50 mL), was dried (sodium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:9) provided 0.68 g (99%) of (±)-(4,5-difluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide as a white solid. Rf=0.93 (silica, ethyl acetate:hexanes 1:9); 1H NMR (DMSO-d6) δH 7.65 (d, 2H); 7.41 (m, 3H); 7.31 (t, 1H); 5.15 (m, 1H); 3.64 (m, 2H); 3.46 (dd, 1H); 3.10 (dd, 1H).

Workup

  1. temperatureto cool
  2. customthe solvent was removed in vacuo
  3. customto provide a crude solid
  4. washwashed with water (50 mL) and aqueous sodium chloride (50 mL)
  5. dry with materialwas dried (sodium sulfate)
  6. customthe solvent was removed in vacuo
  7. customto give a crude solid
  8. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:9)

Sources & evidence

ORD record
ord-8ba1ada7dad84d2ebc994a8ab734035d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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