3-Hydroxybenzaldehyde → 2-Bromo-5-hydroxybenzaldehyde

HRID 1496823Notes

Reaction equation

HRID 1496823 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Br:10]Br>C(O)(=O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 24408Bromine

Product 1

HCID 3871792-Bromo-5-hydroxybenzaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

3-hydroxybenzaldehyde (10 g, 81.9 mmol) was dissolved in glacial acetic acid (50 mL) and cooled at 15° C. To the stirred solution, bromine (15.7 g, 98.2 mmol) was added dropwise while keeping the temperature below 22° C. After overnight stirring at room temperature, the volatiles were removed under vacuum without heating; the residue was co-evaporated three times with hexane (15 mL) and taken up in warm chloroform. Upon cooling, 9.05 g of 2-bromo-5-hydroxybenzaldehyde 3 were obtained as a white solid in two crops. Yield 55%. 1H NMR (300 MHz, CD3COCD3) δ ppm: 10.24 (s, 1H), 9.05 (s, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.34 (d, J=3.1 Hz, 1H), 7.10 (dd, J1=8.7 Hz, J2=3.1 Hz, 1H); 13C NMR (75 MHz, CD3COCD3) δ ppm: 192.8, 159.3, 136.7, 136.2, 125.1, 117.3, 117.2; HRMS (EI) m/z: calcd for C7H5BrO2: 199.9472. found: 199.9463; mp: 132-134° C.

Workup

  1. customthe temperature below 22° C
  2. customthe volatiles were removed under vacuum
  3. temperaturewithout heating
  4. temperatureUpon cooling

Sources & evidence

ORD record
ord-1b3a99f55ee54a87a9cd319fe89231c6
Source dataset
uspto-grants-2015_12
Patent number
US09199936B2

Reaction notes

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