Diboron → HCID 21400433, compound

HRID 1438728Notes

Reaction equation

HRID 1438728 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].B#B>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[CH:7]([OH:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 22759948HCID 22759948, compound

Product 1

HCID 21400433HCID 21400433, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under anhydrous conditions, a stirred solution of 25.0 g (99.5 mmoles) of 5-chloro-2'-fluoro-2-hydroxybenzophenone in 250 ml of anhydrous THF was heated to reflux. The heat source was removed and 115 ml (115 mmoles) of a solution (1M in BH3) of diborane in THF was added rapidly from a dropping funnel; foaming and some refluxing occurred. After addition, external heating was resumed and refluxing was continued for 5 min. A few minutes after heating was resumed, the yellow color of the ketone was discharged. The colorless solution was cooled to room temperature and worked up as described in Example 1a. An oil was obtained in quantitative yield which was used without further purification in the next step.

Workup

  1. customThe heat source was removed
  2. additionAfter addition
  3. temperatureexternal heating
  4. temperaturerefluxing
  5. temperatureA few minutes after heating
  6. customAn oil was obtained in quantitative yield which
  7. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-9ce7c30fe3394f56b2fd42a34331f6af
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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