Hydrogen Bromide → HCID 21470007, compound

HRID 486286Notes

Reaction equation

HRID 486286 reaction equation
[BrH:1].[Br:2][C:3]1[C:4]([OH:13])=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:6]O>C(O)(=O)C>[Br:2][C:3]1[C:4]([OH:13])=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:6][Br:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10911440HCID 10911440, compound

Product 1

HCID 21470007HCID 21470007, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the course of 30 minutes, at room temperature, 20 g of hydrogen bromide are introduced into a suspension of 50 g of 3-bromo-2-hydroxy-5-methoxy-benzyl alcohol in 300 ml of anhydrous acetic acid. The reaction mixture is stirred for 5 hours at room temperature and the resulting solution is concentrated by evaporation. The black-brown oily residue, which crystallises slowly when left to stand at room temperature, is crystallised from ethyl acetate/cyclohexane (5:1) with the addition of a small amount of activated charcoal. 3-Bromo-2-hydroxy-5-methoxy-benzyl bromide is thus obtained [1H-NMR (360 MHz, CDCl3): 3.75 (s, 3H, OCH3), 4.53 (s, 2H, CH2Br), 5.45 (s, 1H, OH), 6.85 (d, 1H), 7.00 (d, 1H) ppm].

Workup

  1. concentrationthe resulting solution is concentrated by evaporation
  2. customThe black-brown oily residue, which crystallises slowly when
  3. waitleft
  4. customto stand at room temperature
  5. customis crystallised from ethyl acetate/cyclohexane (5:1) with the addition of a small amount of activated charcoal

Sources & evidence

ORD record
ord-ac131eb0ebf8417f858ce494a24d952f
Source dataset
uspto-grants-1994_03
Patent number
US05290939

Reaction notes

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