2,3,6-Trimethylphenol → 4-bromo-2,3,6-trimethyl-phenol

HRID 564284Notes

Reaction equation

HRID 564284 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[Br:11]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:11][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([OH:10])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 170162,3,6-TrimethylphenolHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 108225484-bromo-2,3,6-trimethyl-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,3,6-trimethylphenol (40 g; 0.294 mol) in DCM (600 ml) at ambient temperature was added a solution of bromine (16.6 ml; 0.294 mol) in DCM (300 ml) dropwise over 30 mins. Reaction stirred for a further 5 hrs at ambient temperature. A solution of 1M sodium sulfite (300 ml) was added. The layers were separated and the aq. layer extracted with DCM (150 ml). Organics combined, washed with half sat. brine (300 ml), dried (anh. MgSO4), filtered and the solvent evaporated to give a white solid (66.2 g; 105% Th.). 1H NMR (300 MHz, CDCl3), δ/ppm; 2.19 (3H, s, Ar—CH3), 2.22 (3H, s, Ar—CH3), 2.34 (3H, s, Ar—CH3), 7.18 (1H, s, Ar—H).

Workup

  1. customReaction
  2. customThe layers were separated
  3. extractionthe aq. layer extracted with DCM (150 ml)
  4. washwashed with half sat. brine (300 ml)
  5. dry with materialdried (anh. MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customto give a white solid (66.2 g; 105% Th.)

Sources & evidence

ORD record
ord-e5c8146c17b447eab7c65b34c27b51d7
Source dataset
uspto-grants-2011_11
Patent number
US08067642B2

Reaction notes

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