4-Bromophthalic acid → (5-Bromo-2-(hydroxymethyl)phenyl)methanol

HRID 1245057Notes

Reaction equation

HRID 1245057 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11](O)=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH2:11][OH:12])[CH:3]=1

Participants

3

Reactant 1

HCID 814284-Bromophthalic acid

Product 1

HCID 10798791(5-Bromo-2-(hydroxymethyl)phenyl)methanolYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromophthalic acid (3.0 g, 12.24 mmol) in 30 mL of THF was added a solution of borane-THF complex (1.0M) dropwise at 0° C. The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCl (2N) at 0° C. The product was extracted with ethyl acetate and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to afford 2.8 g (100%) of 4-bromo-2-hydroxymethylbenzyl alcohol as a colorless oil. 1H NMR (CDCl3) 7.28 (m, 2H), 7.26 (m, 1H), 4.69 (s, 4H), 2.80 (bs, 2H).

Workup

  1. customThe reaction mixture was quenched by addition of HCl (2N) at 0° C
  2. extractionThe product was extracted with ethyl acetate
  3. washwashed with sat. NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8af30f35727440629e1bc5eeae573e97
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

Loading…