Boron tribromide → 2-(9H-Carbazol-9-yl)-4-methylphenol

HRID 1851343Notes

Reaction equation

HRID 1851343 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[N:14]1[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2>ClCCl>[CH:25]1[C:26]2[N:14]([C:8]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]=3[OH:6])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86710450HCID 86710450, compound

Product 1

HCID 207497772-(9H-Carbazol-9-yl)-4-methylphenolYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.0 M boron tribromide solution in dichloromethane (90 mL, 90 mmol, 1.9 equiv) was added dropwise at −78° C., over 30 minutes, to a solution of compound 4 (13.5 g, 46.98 mmol, 1 equiv) in anhydrous dichloromethane (400 mL). The reaction was warmed to room temperature, when liquid chromatography-mass spectrometry (LCMS) indicated that the reaction was complete. The reaction was quenched with ice-water (200 mL). The layers were separated and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an ANALOGIX 40-150 g column, eluting with a gradient of 0 to 20% ethyl acetate in heptanes to give compound 5 (12.3 g, 95% yield) as a yellow oil.

Workup

  1. customThe reaction was quenched with ice-water (200 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on an ANALOGIX 40-150 g column
  8. washeluting with a gradient of 0 to 20% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-3122eac721e54c099f2f39b594b245d8
Source dataset
uspto-grants-2015_02
Patent number
US08957171B2

Reaction notes

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