3-Hydroxybenzaldehyde → 2-Bromo-3-hydroxybenzaldehyde

HRID 2367981Notes

Reaction equation

HRID 2367981 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C.[Fe]>[Br:15][C:3]1[C:2]([OH:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 37146742-Bromo-3-hydroxybenzaldehydeYield 28%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

The suspension of 3-hydroxybenzaldehyde (5 g, 0.04 mol), iron powder (172 mg, 3 mmol) and sodium acetate (6.72 g, 0.08 mol) in acetic acid (40 mL) was warmed until a clear solution was obtained and then cooled to room temperature. To this mixture was dropwise added a solution of bromine in glacial acetic acid (10 mL) over 15 min. After the addition, the reaction mixture was stirred for 2 h and then poured into ice-water. The resulting mixture was extracted with dichloromethane (3×50 mL). The combined extracts were dried over anhydrous Na2SO4 and concentrated. The residue was re-crystallized from dichloromethane to afford the product (2.3 g, yield 28%). 1H NMR (400 MHz, DMSO-d6 δ 10.30 (s, 1H), 7.54-7.51 (m, 1H), 7.39-7.35 (m, 1H), 7.31-7.27 (m, 1H), 5.90 (s, 1H).

Workup

  1. temperaturewas warmed until a clear solution
  2. customwas obtained
  3. additionAfter the addition
  4. extractionThe resulting mixture was extracted with dichloromethane (3×50 mL)
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was re-crystallized from dichloromethane

Sources & evidence

ORD record
ord-9b8184a41dbb4c2f8450d00ec337a903
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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