Boron tribromide → HCID 58779363, compound

HRID 1372145Notes

Reaction equation

HRID 1372145 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12]([CH:18]=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12]([CH:18]=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58779366HCID 58779366, compound

Product 1

HCID 58779363HCID 58779363, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml round bottom flask a solution of 62.5% pure 4-(4-methoxyphenyl)-1-benzothiophene-7-carbaldehyde (remainder 37.5% 4-(4-methoxyphenyl)-1-benzothiophene-2-carbaldehyde) (102 mg, 0.38 mmol) and CH2Cl2 (2 ml) was cooled to −78° C. Then BBr3 (0.8 ml 1.0 M in CH2Cl2, 0.8 mmol) was added dropwise after which the reaction turned dark red in color. The reaction was allowed to warm to room temperature and after 1 h the reaction was complete by TLC then quenched by pouring into water (15 ml). The mixture was diluted with ether, the layers separated and the aqueous was further extracted with ether. The organic layers were combined, dried over anhydrous Na2SO4, passed through a silica plug and concentrated to a greenish solid. Reverse phase HPLC (CH3CN 0.1% TFA, water 0.1% TFA) afforded 50 mg (52%) desired product as a yellow solid: mp 203–204° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.96 (2H, d, J=8.5 Hz), 7.50 (2H, d, J=8.5 Hz), 7.56 (1H, d, J=5.6 Hz), 7.62 (1H, d, J=7.5 Hz), 7.97 (1H, d, J=5.6 Hz), 8.16 (1H, d, J=7.5 Hz), 9.84 (1H, s), 10.25 (1H, s); MS (ESI) m/z 253 ([M−H])

Workup

  1. customthen quenched
  2. additionby pouring into water (15 ml)
  3. additionThe mixture was diluted with ether
  4. customthe layers separated
  5. extractionthe aqueous was further extracted with ether
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated to a greenish solid

Sources & evidence

ORD record
ord-a2d88abb0c6040ba8df3c6436a0148f9
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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