Lithium Hydroxide → 2-(3,6-dibromo-9H-carbazol-9-yl)acetic acid

HRID 508236Notes

Reaction equation

HRID 508236 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17]([O:19]CC)=[O:18])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[Li+].[OH-]>C1COCC1.CO.O.Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17]([OH:19])=[O:18])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14385110Ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetate

Product 1

HCID 113265512-(3,6-dibromo-9H-carbazol-9-yl)acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of the product of Step 1 (41.1 mg, 0.1 mmol, 1 equiv) in THF-methanol-water (3:2:1, total 1.2 mL) was added LiOH (12.0 mg, 0.5 mmol, 5 equiv). The mixture was stirred at room temperature for 1 hour. The reaction was diluted with 1M HCl (10 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with water (10 mL) twice and dried with MgSO4 to afford 38.3 mg white solid as product, yield 99%. 1H NMR (CDCl3, 400 MHz) δ=5.02 (s, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.58 (dd, J=8.7, 1.2 Hz, 2H) 8.16 (d, J=1.6 Hz, 2H). ESI (m/z): 379.6 (M−H+).

Workup

  1. extractionextracted with ethyl acetate (10 mL)
  2. washThe organic layer was washed with water (10 mL) twice
  3. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-abb7a75f3a4e4836b8e718ed021a7f6b
Source dataset
uspto-grants-2015_08
Patent number
US09095572B2

Reaction notes

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