Benzyl Bromide → HCID 68583368, compound

HRID 13939Notes

Reaction equation

HRID 13939 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([Cl:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:15])[CH:2]=[CH2:3].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[CH:13]=[C:12]([Cl:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[O:15][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11579428HCID 11579428, compound

Product 1

HCID 68583368HCID 68583368, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-allyl-4-chloro-1-naphthol (20.0 g, 0.091 mol) in N,N-dimethylformamide (700 mL) was added sodium hydride (60 wt. %, 4.39 g, 0.11 mol) and the reaction mixture was allowed to stir at room temperature for 30 min. Benzyl bromide (18.8 g, 0.11 mol) was then added and the reaction mixture was allowed to stir at room temperature for 2 h. The solvent was removed in vacuo to provide a crude oil. The residue was re-dissolved in ethyl acetate (500 mL) and the organic layer was washed with water (2×250 mL), saturated aqueous sodium chloride (250 mL), dried (sodium sulfate) and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, dichloromethane:hexanes 1:4) provided 23.0 g (82%) of 2-allyl-1-(benzyloxy)4-chloronaphthalene as a light brown oil. Treatment of the benzyl ether with AD-mix-α (104.3 g) generally according to the procedure described for Intermediate 2 afforded 24.0 g (94%) of (±)-3-[1-(benzyloxy)-4-chloro-2-naphthyl]propane-1,2-diol as a white solid. mp 69-71° C.; Anal. calcd. for C20H19ClO: C, 70.07; H, 5.59. Found: C, 68.01; H, 5.47.

Workup

  1. stirringto stir at room temperature for 2 h
  2. customThe solvent was removed in vacuo
  3. customto provide a crude oil
  4. washthe organic layer was washed with water (2×250 mL), saturated aqueous sodium chloride (250 mL)
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent was removed in vacuo
  7. customto provide a crude oil
  8. customPurification by flash column chromatography (silica, dichloromethane:hexanes 1:4)

Sources & evidence

ORD record
ord-c9563bbfca8c4f828b3517d243eb00ac
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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