Hydrochloric Acid → HCID 117965873, compound

HRID 2170925Notes

Reaction equation

HRID 2170925 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C@H:6]2[O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([CH2:24]Cl)=[CH:18][C:19](=[O:23])[O:20]2)=[CH:15][CH:14]=1.BrC1C(C)=CC([O:31]CCC(C)(O)C)=CC=1C.[OH-].[Na+].Cl>CCO.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C@H:6]2[O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:17]([CH2:18][C:19]([OH:31])=[O:23])=[CH:24][O:20][C:21]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679729214-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-olHCID 117965950HCID 117965950, compound

Product 1

HCID 117965873HCID 117965873, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 15.0 g (35.4 mmol) 7-((R)-4-bromo-7-fluoroindan-1-yloxy)-4-chloromethyl-chromen-2-one (product from step 2) in 45 ml EtOH, 9.29 ml (177 mmol) aq. NaOH (50%) is added. The funnel is rinsed with 50 ml water and the mixture is heated to reflux for approx. 0.5 h. Then, over a time period of 30 min a mixture of 30 ml water and 14.7 ml (177 mmol) conc. HCl (37%) is added. The suspension is cooled to r.t., the product is filtered off, washed with EtOH/water (1:1, 2×30 ml) and dried. Yield: 14.0 g; Rf=0.38 (silica gel, PE/EtOAc/AcOH=6/4/0.1); Mass spectrum (ESI): m/z=405 [M+H]+.

Workup

  1. washThe funnel is rinsed with 50 ml water
  2. temperaturethe mixture is heated
  3. temperatureto reflux for approx. 0.5 h
  4. additionis added
  5. filtrationthe product is filtered off
  6. washwashed with EtOH/water (1:1, 2×30 ml)
  7. customdried

Sources & evidence

ORD record
ord-4a218452b08f4d9b94a215c154e7fbd5
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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