Boron tribromide → 4-(2-Methylindol-1-yl)phenol

HRID 491017Notes

Reaction equation

HRID 491017 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]2[CH3:18])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[CH3:18][C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[C:17]2[C:12]([CH:11]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 120796281-(4-Methoxyphenyl)-2-methyl-1H-indole

Product 1

HCID 576757604-(2-Methylindol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Methoxyphenyl)-2-methyl-1H-indole (175 mg, 0.73 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0° C. Boron tribromide (2.19 mL, 1 M solution in dichloromethane, 2.19 mmol) was added dropwise, and the reaction was stirred for 2 hours. The reaction was quenched by addition of saturated sodium bicarbonate solution, then extracted with dichloromethane followed by ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The reaction was assumed to be quantitative. LC-MS (C15H13NO calc'd 223) m/z 224 (M+H).

Workup

  1. customThe reaction was quenched by addition of saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a6c6f985a9246b1b454f50df5668674
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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