4-Fluorophenol → HCID 68931920, compound

HRID 898347Notes

Reaction equation

HRID 898347 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9](O)[CH2:8][CH2:7][CH2:6][C:5]2=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([O:23][C:20]1[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=1)[C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 597396HCID 597396, compound

Product 1

HCID 68931920HCID 68931920, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-ol (50 mg, 0.19 mmol) in THF (5 mL) was added p-fluorophenol (43 mg, 0.38 mmol), polymer supported triphenylphosphine (1.67 mmol/g, 228 mg, 0.38 mmol) and diisopropyl azodicarboxylate (77 mg, 0.38 mmol). The reaction was stirred at room temperature for 16 h, and additional diisopropyl azodicarboxylate (77 mg, 0.38 mmol) was added. The reaction was stirred for 16 h, filtered and concentrated. The crude product was purified by flash chromatography on silica (2% to 20% ethyl acetate/hexanes gradient) to provide 6-bromo-N-(4-fluorophenoxy)-2,3,4,9-tetrahydro-1H-carbazole (8 mg, 12%) as a white solid: 1H-NMR (DMSO-d6): δ 11.20 (s, 1H), 7.61 (d, 1H), 7.26 (d, 1H), 7.16-7.06 (m, 5H), 5.53 (t, 1H), 2.75-2.69 (m, 1H), 2.57-2.50 (m, 1H), 2.02-1.76 (m, 4H).

Workup

  1. stirringThe reaction was stirred for 16 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica (2% to 20% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-8bac594e5ad3474a885add588d19d3d4
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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