Hydrochloric Acid → HCID 20436029, compound

HRID 1154077Notes

Reaction equation

HRID 1154077 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10]C.[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl.BrC1C(OC)=CC(O)=C(C=1)C(C1C=CC=CC=1F)=O>>[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[C:15]([C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=1[F:12])=[O:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 6122962-Bromo-1,3-dimethoxybenzeneHCID 6451240Aluminum(III) ChlorideHCID 20150577HCID 20150577, compound

Product 1

HCID 20436029HCID 20436029, compound

Procedure

2-bromo-1,3-dimethoxybenzene (217 g; 1.0 mole) and 2-fluorobenzoyl chloride (158 g; 1.0 mole) are dissolved in 1,2-dichorothane and aluminum chloride (133 g; 1,0 mole) is added slowly. The reaction mixture is refluxed for 2 hours and then worked up with 5% hydrochloric acid. In this way a 1:2 mixture of 5-bromo-2'-fluoro-2-hydroxy-4-methoxybenzophenone and 3-bromo-2'fluoro-2-hydroxy-4-methoxybenzophenone is obtained, as indicated by nuclear magnetic resonance (NMR). A quantity of this mixture is separated by preparative high pressure liquid chromatography into its two components, 5-bromo-2'-fluoro-2-hydroxy-4-methoxybenzophenone, m.p. 127°-129° C. and 3-bromo-2'-fluoro-2-hydroxy-4-methoxybenzophenone, m.p. 137°-139° C.

Workup

  1. additionis added slowly
  2. temperatureThe reaction mixture is refluxed for 2 hours

Sources & evidence

ORD record
ord-7db4a9e4b2f54a7a8fb88fcb3f89e6a2
Source dataset
uspto-grants-1984_12
Patent number
US04487934

Reaction notes

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