Monobenzone → 2-Bromo-4-(phenylmethoxy)phenol

HRID 1420684Notes

Reaction equation

HRID 1420684 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]Br>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[C:13]([Br:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7638MonobenzoneHCID 24408Bromine

Product 1

HCID 109788072-Bromo-4-(phenylmethoxy)phenolYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of 4-benzyloxyphenol (30 g, 150 mmol) in chloroform (400 ml) was added, dropwise, a solution of bromine (24 g, 150 mmol) in chloroform (150 ml). After stirring for 1 hour the mixture was washed with 0.1M NaHSO3 (500 ml), then water (500 ml). The chloroform layer was separated, dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 5, 10, 20% ethyl acetate/hexane. Recrystallisation from hexane afforded the title compound (20.5 g, 49%); δH (250MHz, CDCl3) 4.98 (2H, s, OCH2), 6.82--6.99 (2H, m, ArH), 7.09-7.12 (1H, d, J 2.75Hz, ArH), 7.30-7.42 (5H, m).

Workup

  1. additionwas added
  2. washwas washed with 0.1M NaHSO3 (500 ml)
  3. customThe chloroform layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 5, 10, 20% ethyl acetate/hexane
  8. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-111ac8edee5448d79f623e42f27ff677
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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