Bromine → 2-Bromo-4-cyclopentoxy-3-hydroxy-benzaldehyde

HRID 131588

Reaction equation

HRID 131588 reaction equation
[CH:1]1([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=2[OH:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].[Br:21]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.[Fe]>[Br:21][C:9]1[C:8]([OH:15])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 24408BromineHCID 517045Sodium AcetateHCID 167261494-Cyclopentyloxy-3-hydroxybenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 211057072-Bromo-4-cyclopentoxy-3-hydroxy-benzaldehydeYield 58%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
15 °C

Procedure

4-cyclopentoxy-3-hydroxy-benzaldehyde (1.0 gm, 4.84 mmol) was dissolved in glacial acetic acid (20 ml). Anhydrous sodium acetate (0.8 gm, 9.7 mmol) was added to the above solution followed by powdered iron (0.022 gm). The system was flushed thoroughly with nitrogen. A solution of bromine (0.854 gm, 5.32 mmol) in glacial acetic acid (10 ml) was added to the above stirred suspension at 15° C. over a period of 15 min. The reaction mixture was stirred at 15° C. for 45 min. The reaction mixture was poured into aqueous 2% sodium bisulfite (100 ml) and stirred for 10 min. The precipitate was filtered washed with water (100 ml), and dried to obtain 800 mg of 2-bromo-4-cyclopentoxy-3-hydroxy-benzaldehyde as white powder mp: 107-109° C.

Workup

  1. customThe system was flushed thoroughly with nitrogen
  2. stirringstirred for 10 min
  3. filtrationThe precipitate was filtered
  4. washwashed with water (100 ml)
  5. customdried

Sources & evidence

ORD record
ord-5424996d56024a2782ce8d3a48d3dd08
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Linked notes

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