Benzyl Bromide → HCID 18433467, compound

HRID 2306184Notes

Reaction equation

HRID 2306184 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:20]([O:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[CH:11][CH:10]=[C:9]2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:14][CH:15]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18433467HCID 18433467, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(tert-butoxycarbonylamino)-2-naphthol, as described above in Step A, (93 mg, 0.36 mmol), benzyl bromide (64 mg, 0.37 mmol), and Cs2CO3 (146 mg, 0.45 mmol) in dry DMF (3 mL) was stirred, under argon, at ambient temperature for 18 hours. The reaction mixture was poured into saturated aqueous NaHCO3 (15 mL) and EtOAc (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—5 to 15% diethyl ether to yield the desired product as a pale solid.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography on silica
  5. washeluting with a gradient of hexane—5 to 15% diethyl ether

Sources & evidence

ORD record
ord-307b2aee66ef4705b7188cf689d2ee25
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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