Sodium Hydroxide → 7-Chloro-1,6-dihydroxynaphthalene

HRID 1047349

Reaction equation

HRID 1047349 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[O:12]C)=[CH:4][C:3]=1[O:14]C.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[OH:12])=[CH:4][C:3]=1[OH:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 587051697-Chloro-1,6-dimethoxynaphthalene

Product 1

HCID 578928847-Chloro-1,6-dihydroxynaphthaleneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 50 ml round bottom flask equipped with magnetic stirring bar was charged with solution of compound 47 (2.0 g, 9.0 mmol) in anhydrous CH2Cl2 (20 ml). Flask was filled in with argon atmosphere and BBr3 (9.0 g, 3.39 ml, 36.0 mmol) was added through a syringe over 5 min. Resultant mixture was magnetically stirred overnight at room temperature. Reaction mixture was carefully poured into ice-water mixture (30 g), diluted with CH2Cl2 and neutralized by addition of 2% NaOH (pH˜6-7). Organic phase was separated, washed with NaHCO3 (2×10 ml) and NaCl (20 ml) solutions, dried over MgSO4 and concentrated in vacuum to give desired product 48 (1.54 g, 7.9 mmol, 88% yield) as fluffy off-white solid. 1H NMR (DMSO-d6): δ 10.45 (s, 1H), 10.13 (s, 1H), 8.04 (s, 1H), 7.23-7.10 (m, 3H), 6.67 (d, J=7.3 Hz, 1H).

Workup

  1. customA 50 ml round bottom flask equipped with magnetic stirring bar
  2. additionwas added through a syringe over 5 min
  3. customReaction mixture
  4. customOrganic phase was separated
  5. washwashed with NaHCO3 (2×10 ml) and NaCl (20 ml) solutions
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-40ac595e22814f9fb69d30ed5cfd65a4
Source dataset
uspto-grants-2013_10
Patent number
US08569516B2

Linked notes

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