Phenol → HCID 86710600, compound

HRID 1027203Notes

Reaction equation

HRID 1027203 reaction equation
C1(O)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:14]([O:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][C:28]([OH:32])=[CH:29]2)=[CH:24][C:23]=1[Br:33])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Br[CH2:35][CH2:36][CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[Na+].[I-]>CC(C)=O.CCOC(C)=O>[CH2:14]([O:21][C:22]1[C:23]([Br:33])=[CH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([O:32][CH2:35][CH2:36][CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[CH:27][CH:26]=2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 748928202-(Benzyloxy)-3-bromo-7-naphthol

Product 1

HCID 86710600HCID 86710600, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Following GENERAL METHOD 5-1 for phenol alkylation, Cs2CO3 (485 mg, 1.489 mmol) was added to a solution of 7-(benzyloxy)-6-bromonaphthalen-2-ol (490 mg, 1.489 mmol) in acetone (14.90 mL) at RT. The reaction mixture was stirred for 5 min then ((3-bromopropoxy)methyl)benzene (682 mg, 2.98 mmol) was added, followed by addition of NaI (446 mg, 2.98 mmol). The reaction mixture was heated to 60° C. and stirred overnight, then filtered, washed with acetone and concentrated in vacuo. The resulting residue was partitioned between Et2O (60 mL) and water (20 mL). After separation, the organic layer was washed with saturated aq. sodium sulfite solution (20 mL), 2 M Na2CO3, and brine. The organic layer was then dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (10-60% EtOAc/heptane) afforded 3-(benzyloxy)-6-(3-(benzyloxy)propoxy)-2-bromonaphthalene (422 mg, 0.884 mmol, 60% yield) as a white solid (eluting at 30% EtOAc). LCMS Rt=1.81 min (condition C); LCMS (M+1)=479.9.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered
  3. washwashed with acetone
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was partitioned between Et2O (60 mL) and water (20 mL)
  6. customAfter separation
  7. washthe organic layer was washed with saturated aq. sodium sulfite solution (20 mL), 2 M Na2CO3, and brine
  8. dry with materialThe organic layer was then dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customSilica gel chromatography (10-60% EtOAc/heptane) afforded

Sources & evidence

ORD record
ord-30b2cd6d0bc647359469a82493569f6d
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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