Bromine → HCID 10207413, compound

HRID 1278813Notes

Reaction equation

HRID 1278813 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([C:10]2[C:22]3[C:21]([CH3:23])=[C:20]([CH3:24])[S:19][C:18]=3[C:17]([Br:25])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:7]=[CH:6][C:5]=1[OH:26])([CH3:3])[CH3:2].C([O-])(=O)C.[K+].[Br:32]Br>C(O)(=O)C>[Br:32][C:6]1[CH:7]=[C:8]([C:10]2[C:22]3[C:21]([CH3:23])=[C:20]([CH3:24])[S:19][C:18]=3[C:17]([Br:25])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[OH:26]

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 15490891HCID 15490891, compound

Product 1

HCID 10207413HCID 10207413, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a suspension of 2-isopropyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (0.35 g, 0.81 mmol) and potassium acetate (0.80 g, 8.11 mmol) in glacial acetic acid (11 mL) was added a solution of bromine (0.05 mL, 0.97 mmol) in glacial acetic acid (1.5 mL) dropwise at room temperature. An additional 1 mL of acetic acid was used to rinse the pipette and flask. After stirring at room temperature for 4 h the reaction was quenched with a small amount of dilute sodium bisulfite and diluted with water (100 mL). The white solid was collected on a sintered glass funnel, washed well with water and dried (Na2SO4) to give the title compound as a white solid (0.40 g,98%): mp 157-162° C.; (DMSO-d6): δ 9.20 (s, 1H), 8.19 (d, 1H), 7.66-7.61 (m, 1H), 7.49-7.48 (m, 2H), 7.35 (d, 1H), 7.13 (d,1H), 3.40 (septet, 1H), 2.42 (s, 3H), 1.60 (s, 3H), 1.16 (d, 6H); MS(+FAB): [M+H], 2 bromine isotope pattern, 502 (12%), 504 (30%), 506 (18%); Anal. Calc. for C23H20Br2OS: C, 54.78, H, 4.00, N, 0.00. Found: C, 53.67, H; 3.84, N, 0.03.

Workup

  1. washto rinse the pipette and flask
  2. customwas quenched with a small amount of dilute sodium bisulfite
  3. additiondiluted with water (100 mL)
  4. customThe white solid was collected on a sintered glass funnel
  5. washwashed well with water
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-fa01e5d04c3a4918aac3b312d2f89602
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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