Boron tribromide → 6-Decyl-3-methylthio-2-hydroxynaphthalene

HRID 1476372Notes

Reaction equation

HRID 1476372 reaction equation
[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([O:21]C)[C:15]([S:23][CH3:24])=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].B(Br)(Br)Br>ClCCl>[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([OH:21])[C:15]([S:23][CH3:24])=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 867043856-Decyl-3-methylthio-2-methoxynaphthalene

Product 1

HCID 867043886-Decyl-3-methylthio-2-hydroxynaphthaleneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane (50 ml) solution of 6-decyl-3-methylthio-2-methoxynaphthalene (compound (4)-64) (28 g, 81 mmol) was added to a dichloromethane solution of BBr3 (ca.2 M 70 ml, 140 mmol) at −78° C. The solution was stirred at room temperature for 12 hours. Ice (approximately 20 g) was added to the mixture. The reaction solution was extracted with dichloromethane (20 ml×3). The organic layers obtained by repeating the extraction three times were collected, washed with saturated saline water (30 ml×3), dried with MgSO4, and condensed. The residue was refined by column chromatography (silica gel, developed at dichloromethane:hexane=1:1), and recrystallized with hexane to obtain 6-decyl-3-methylthio-2-hydroxynaphthalene (18.1 g, 72%) as white crystals.

Workup

  1. extractionThe reaction solution was extracted with dichloromethane (20 ml×3)
  2. customThe organic layers obtained
  3. extractionthe extraction three times
  4. customwere collected
  5. washwashed with saturated saline water (30 ml×3)
  6. dry with materialdried with MgSO4, and condensed
  7. customrecrystallized with hexane

Sources & evidence

ORD record
ord-73db2048707047afbebf29527f8ae1ca
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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