5-Bromonaphthalene-2-carboxylic acid → HCID 13477023, compound

HRID 330255Notes

Reaction equation

HRID 330255 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12](O)=[O:13])=[CH:7]2>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][OH:13])=[CH:7]2

Participants

3

Reactant 1

HCID 149606465-Bromonaphthalene-2-carboxylic acid

Product 1

HCID 13477023HCID 13477023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromonaphthalene-2-carboxylic acid (10.04 g, 40 mmol) in dry THF (400 mL) cooled to 0° C. was added BH3 ·THF (54 mL, 54 mmol; 1.0M solution in THF) dropwise over 45 minutes. The resulting solution was stirred overnight while warming to room temperature. The excess BH3 was quenched by the addition of H2O (200 mL) at 0° C. and the volatiles were removed in vacuo. The aqueous residue was extracted with Et2O (2×250 mL) and the combined organic layers were dried (MgSO4) and concentrated in vacuo to give the title compound as a colorless liquid which solidified to a white solid upon standing (9.48 g, 100%). This material was of adequate purity to be used as such in the next step.

Workup

  1. customThe excess BH3 was quenched by the addition of H2O (200 mL) at 0° C.
  2. customthe volatiles were removed in vacuo
  3. extractionThe aqueous residue was extracted with Et2O (2×250 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2beab8e882734413aa1b25f4914e2302
Source dataset
uspto-grants-1990_01
Patent number
US04895861

Reaction notes

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