Hydrogen Bromide → 1-(Bromomethyl)-2-phenoxybenzene

HRID 736030Notes

Reaction equation

HRID 736030 reaction equation
[BrH:1].[O:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[Br:1][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 36601112-Phenoxybenzyl alcohol

Product 1

HCID 226754691-(Bromomethyl)-2-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 2-Phenoxy-benzoic acid (1 g, 4.67 mmol), in several portions, to a suspension of Lithium aluminium hydride (372 mg, 9.33 mmol) in dry THF (20 ml) at room temperature and stir. After 1 h, add aqueous 1M HCl dropwise carefully, then pour into H2O and extract three times with Et2O. Combine the organic phases, dry over Na2SO4 and concentrate at vacuum to yield pure (2-Phenoxy-phenyl)-methanol as courless oil. Add aqueous concentrated HBr (16 ml) to a solution of (2-Phenoxy-phenyl)-methanol (900 mg, 4.5 mmol) in CH2Cl2 (5 ml) and stir at room temperature. After 1 h. separate the organic phase and wash the aqueous one with CH2Cl2. Combine organic phases, wash with H2, dry over Na2SO4 and concentrate at vacuum to obtain a residue. Purify the residue by column chromatography on silica gel eluting with hexane:CH2Cl2, 2:1 to afford 1-Bromomethyl-2-phenoxy-benzene as colourless oil. 1H-NMR (CDCl3, 200 MHz): δ 7.44-7.01 (m, 8H), 6.84 (d, J=1.2 and 8.0 Hz, 1H), 4.60 (s, 2H).

Workup

  1. customAfter 1 h. separate the organic phase
  2. washwash the aqueous one with CH2Cl2
  3. washCombine organic phases, wash with H2
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate at vacuum
  6. customto obtain a residue
  7. customPurify the residue by column chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-08580c270cdc48a29cb13a1840380e99
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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