Sodium hydride → Methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester

HRID 1513863Notes

Reaction equation

HRID 1513863 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([OH:21])=[C:16]([Br:22])[CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([O:21][S:24]([CH3:23])(=[O:26])=[O:25])=[C:16]([Br:22])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 670051586-Benzyloxy-2-bromo-naphthalen-1-ol

Product 1

HCID 86626526Methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl esterYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add sodium hydride (24 g, 0.6 mmol) portionwise to a solution of 6-benzyloxy-2-bromo-naphthalen-1-ol (179 g, 0.54 mol) in THF (3.0 L) at 0° C. Add methanesulfonyl chloride (47 mL, 0.61 mol) over 45 minutes and stir the reaction for 1.5 hours at 10° C. Add sodium bicarbonate solution (500 mL) and water (500 ml). Separate the layers and extract the aqueous layer with ethyl acetate (500 mL×2). Combine the organic layers and wash with brine (200 mL). Dry with magnesium sulfate, filter and concentrate in vacuo. Triturate the residue by adding 20% ethyl acetate in hexane (1 L) to obtain a solid. Filter, wash the solid with toluene (200 mL×2) and dry the solid to get 176 g (80%) of methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester.

Workup

  1. customthe reaction for 1.5 hours at 10° C
  2. customSeparate the layers
  3. extractionextract the aqueous layer with ethyl acetate (500 mL×2)
  4. washCombine the organic layers and wash with brine (200 mL)
  5. dry with materialDry with magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customTriturate the residue
  9. additionby adding 20% ethyl acetate in hexane (1 L)
  10. customto obtain a solid
  11. filtrationFilter
  12. washwash the solid with toluene (200 mL×2)
  13. customdry the solid

Sources & evidence

ORD record
ord-d021aabcd5e64dc3b3e158efbe6901b6
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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