Borane;tetrahydrofuran → 8-Bromo-2-hydroxymethylnaphthalene

HRID 1089576Notes

Reaction equation

HRID 1089576 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12](O)=[O:13])[CH:8]=[CH:7]2.B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([CH2:12][OH:13])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 146963788-Bromonaphthalene-2-carboxylic acid

Product 1

HCID 146963798-Bromo-2-hydroxymethylnaphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of 8-bromo-2-naphthoic acid (2.25 g, 8.96 mmol) in THF (12 mL) was added BH3.THF (1M in THF, 12.5 mL, 12.50 mmol) over 20 minutes. The cooling bath was removed and stirring was continued at room temperature overnight. The mixture was recooled to 0° C. and saturated aqueous K2CO3 (8 mL) was added. H2O (10 mL) was added and the mixture was extracted with ether. The combined extracts were washed with saturated aqueous NaCl, dried (MgSO4) and concentrated. The crude product was recrystallized from ether/hexane to give an off-white solid (1.70 g, 80%), m.p. 110°-111° C.

Workup

  1. customThe cooling bath was removed
  2. stirringstirring
  3. customwas recooled to 0° C.
  4. additionsaturated aqueous K2CO3 (8 mL) was added
  5. additionH2O (10 mL) was added
  6. extractionthe mixture was extracted with ether
  7. washThe combined extracts were washed with saturated aqueous NaCl
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe crude product was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-9854039944b849dfb10cdb3dfcec850f
Source dataset
uspto-grants-1990_10
Patent number
US04966975

Reaction notes

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