Boron tribromide → 2-Chloro-3-fluoro-4-nitrophenol

HRID 2279046Notes

Reaction equation

HRID 2279046 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([F:18])[C:10]=1[Cl:19])C1C=CC=CC=1.BrB(Br)Br>C(Cl)Cl>[Cl:19][C:10]1[C:11]([F:18])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 904268951-(Benzyloxy)-2-chloro-3-fluoro-4-nitrobenzene

Product 1

HCID 702152852-Chloro-3-fluoro-4-nitrophenolYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of 1-(benzyloxy)-2-chloro-3-fluoro-4-nitrobenzene (45 g, 160 mmol) in DCM (200 mL) was treated drop-wise with tribromoborane (7.9 g, 320 mmol) over 0.5 h, stirred at 0° C. for 2 h, treated with satd. NaHCO3 and was washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 2-chloro-3-fluoro-4-nitrophenol (25 g, 82%). 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1 H), 6.95 (m, 2 H), 4.67 (brs, 2H).

Workup

  1. additiontreated with satd
  2. washNaHCO3 and was washed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8c5e6bd2064849ba4cc6a8ea6fda36
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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