HCID 18415136, compound → HCID 18415137, compound

HRID 991975Notes

Reaction equation

HRID 991975 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)[C:5](OC)=[O:6]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:22])[CH3:23])[CH:14]=1)[CH2:5][OH:6]

Participants

3

Reactant 1

HCID 18415136HCID 18415136, compound

Product 1

HCID 18415137HCID 18415137, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-dibromo-4-(4-methoxy-3-isopropyl-phenoxy)-benzoate (Example 1a) (4.6 g) was treated with a 1 M solution of diisobutyl aluminium hydride(DIBAL) in THF (40 ml) at 0° C. and then warmed to room temperature and stirred for 1 hour. The reaction mixture was poured into an ice-cold 1 M HCl solution and extracted with ethyl acetate 3 times. The organic layer was washed (brine), dried, filtered and concentrated to dryness affording 3,5-dibromo-4-(4-methoxy-3-isopropylphenoxy)benzylalcohol (4.15 g, 96%) as oil which became a white solid after standing.

Workup

  1. extractionextracted with ethyl acetate 3 times
  2. washThe organic layer was washed (brine)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-99ebfcf9115f45a29e30a2363ce444c6
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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