Water → Neopentyl 5-bromonaphthalene-2-sulfonate

HRID 234778Notes

Reaction equation

HRID 234778 reaction equation
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([S:18](Cl)(=[O:20])=[O:19])=[CH:13]2.C1(C)C=CC=CC=1.O>N1C=CC=CC=1>[Br:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([S:18]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])(=[O:19])=[O:20])=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6404Neopentyl alcoholHCID 109577165-bromonaphthalene-2-sulfonyl Chloride

Product 1

HCID 10948283Neopentyl 5-bromonaphthalene-2-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Solid neopentyl alcohol (2.7 grams; 30.8 mmol) was added at room temperature to a solution of 5-bromonaphthalene-2-sulfonyl chloride (8.5 grams; 28 mmol) in 40 mL of pyridine. The reaction mixture was stirred at room temperature overnight (about 16 hours). The reaction mixture was co-distilled with toluene (about 100 mL) and the resulting oil poured into water to give a pale yellow solid which was filtered and dried. The solid was further purified by silica gel chromatography (EtOAc: Hexane 1:8). Yield: 8.9 gm (89%).

Workup

  1. customto give a pale yellow solid which
  2. filtrationwas filtered
  3. customdried
  4. customThe solid was further purified by silica gel chromatography (EtOAc: Hexane 1:8)

Sources & evidence

ORD record
ord-70c42bfd9a41471d952628f8d0057a12
Source dataset
uspto-grants-1997_01
Patent number
US05596095

Reaction notes

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