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

HRID 2264681Notes

Reaction equation

HRID 2264681 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-fa97a77756ae4ba7a815112537837e8d
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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