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

HRID 62171Notes

Reaction equation

HRID 62171 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-50ac9f11acb64bdfaceeee7966ffa37d
Source dataset
uspto-grants-2016_09
Patent number
US09446022B2

Reaction notes

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