Hydrochloric Acid → HCID 59410089, compound

HRID 2404878Notes

Reaction equation

HRID 2404878 reaction equation
C(=O)([O-])OC[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Br:13])=[CH:6][C:5]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-:22].[K+].Cl>CO>[Br:13][C:7]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]([OH:22])=[C:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68464338HCID 68464338, compound

Product 1

HCID 59410089HCID 59410089, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4-bromo-2-cyclohexyl-5-nitro-phenyl)methyl carbonate (1.5 g, 4.2 mmol) in methanol (15 mL) was added KOH (353 mg, 6.3 mmol) portionwise at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and stirred for 3 h. The reaction mixture was acidified with 1N HCl. The solvent was evaporated and water was added. The aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to give 4-bromo-2-cyclohexyl-5-nitrophenol (1.2 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.50 (s, 1H), 7.39 (s, 1H), 5.10 (s, 1H), 2.90-2.83 (m, 1H), 1.91-1.89 (m, 4H), 1.83-1.80 (m, 1H), 1.51-1.24 (m, 5H)

Workup

  1. additionAfter addition
  2. customThe solvent was evaporated
  3. additionwater was added
  4. extractionThe aqueous layer was extracted with DCM (3×10 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-537d387b83ab4981a704c16778eefc0b
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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